Aryl-alkyne compounds as herbicides

ABSTRACT

Compounds of formula (I) wherein Q is a group formula (II), (III); Z is ═N—, formula (IV) or ═C(R 2 )—; n is 0, 1, 2 or 3; R 3  or R 4  are each independently of the other hydrogen, alogen, —CN, C 1 -C 4 alkyl or C 1 -C 4 alkoxyl; or R 3  and R 4  together are C 2 -C 5 alkylene; and the agrochemically acceptable salts and all stereoisomers and tautomers of the compounds of formula (I) are suitable for use as herbicides.

The present invention relates to novel, herbicidally active phenyl- andpyridyl-alkynes, to processes for their preparation, to compositionscomprising those compounds, and to their use in controlling weeds,especially in crops of useful plants, or in inhibiting plant growth.

Phenylalkynes having herbicidal action are described, for example, inJP-A-1 1147 866, WO 01/55066 and WO 02/28182.

Novel phenyl- and pyridyl-alkynes that have herbicidal andgrowth-inhibiting properties have now been found.

The present invention accordingly relates to compounds of formula I

wherein

-   Q is a group-   Z is ═N—,-    or ═C(R₂)—;-   n is 0, 1, 2 or 3;-   each R, independently is halogen, —CN, —SCN, —SF₅, —NO₂, —NR₅R₆,    —CO₂R₇, —CONR₈NR₉, —C(R₁₀)═NOR₁₁, —COR₁₂, —OR₁₃, —SR₁₄, —SOR₁₅,    —SO₂R₁₆, —OSO₂R₁₇, C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl or    C₃-C₆cycloalkyl; or is C₁-C₈alkyl, C₂-C₈alkenyl or C₂-C₈alkynyl    mono- to penta-substituted by halogen or mono-, di- or    tri-substituted by —CN, —NO₂, —NR₁₈R₁₉, —CO₂R₂₀, —CONR₂₁R₂₂, —COR₂₃,    —C(R₂₄)═NOR₂₅, —C(S)NR₂₆R₂₇, —C(C₁-C₄alkylthio)═NR₂₈, —OR₂₉, —SR₃₀,    —SOR₃₁, —SO₂R₃₂ or by C₃-C₆cycloalkyl; or-   each R₁ independently is C₃-C₆cycloalkyl mono- to penta-substituted    by halogen or mono-, di- or tri-substituted by —CN, —NO₂, —NR₁₈R₁₉,    —CO₂R₂₀, —CONR₂₁R₂₂, —COR₂₃, —C(R₂₄)═NOR₂₅, —C(S)NR₂₆R₂₇,    —C(C₁-C₄alkylthio)═NR₂₈, —SR₃₀, —SOR₃₁, —SO₂R₃₂ or by    C₃-C₆cycloalkyl; or-   each R₁ independently is phenyl which may in turn be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or,-   when Q is a group Q₁, Q₂, Q₃ or Q₅, two adjacent R₁ substituents may    together form a C₁-C₇alkylene bridge which may be interrupted by    from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur    and which may be mono- to penta-substituted by halogen or by    C₁-C₆alkyl or mono-, di- or tri-substituted by C₁-C₆alkoxy, the    total number of ring atoms being at least 5 and at most 9; or,-   when Q is a group Q₁, Q₂, Q₃ or Q₅, two adjacent R₁ substituents may    together form a C₂-C₇alkenylene bridge which may be interrupted by    from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur    and which may be mono- to penta-substituted by halogen or by    C₁-C₆alkyl or mono-, di- or tri-substituted by C₁-C₆alkoxy, the    total number of ring atoms being at least 5 and at most 9;-   R₃ or R₄ are each independently of the other hydrogen, halogen, —CN,    C₁-C₄alkyl or C₁-C₄alkoxy; or-   R₃ and R₄ together are C₂-C₅alkylene;-   R₅ is hydrogen or C₁-C₈alkyl;-   R₆ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    benzyl, it being possible for phenyl and benzyl in turn to be mono-    to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₅ and R₆ together are a C₂-C₅alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₇ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl mono- to penta-substituted    by halogen or mono-, di- or tri-substituted by C₁-C₄alkoxy or by    phenyl, it being possible for phenyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₈ is hydrogen or C₁-C₈alkyl;-   R₉ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN, or-   R₉ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₈ and R₉ together are C₂-C₅alkylene;-   R₁₀ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₁ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₁₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₃ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl; or-   R₁₃ is phenyl or phenyl-C₁-C₆alkyl, it being possible for the phenyl    ring in turn to be mono- to penta-substituted by halogen or by    C₁-C₄alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,    C₁-C₄alkoxy, —CN, —NO₂, C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by    C₁-C₈alkylsulfonyl, or-   R₁₃ is C₁-C₈alkyl mono- to penta-substituted by halogen or mono-,    di- or tri-substituted by —CN, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino    or by C₁-C₄alkoxy;-   R₁₄ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl mono- to penta-substituted by halogen or mono-, di- or    tri-substituted by —CN or by C₁-C₄alkoxy;-   R₁₅, R₁₆ and R₁₇ are each independently of the others C₁-C₈alkyl,    C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono- to    penta-substituted by halogen or mono-, di- or tri-substituted by —CN    or by C₁-C₄alkoxy;-   R₁₈ is hydrogen or C₁-C₈alkyl;-   R₁₉ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    benzyl, it being possible for phenyl and benzyl in turn to be mono-    to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₁₈ and R₁₉ together are a C₂-C₆alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₂₀ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    benzyl, it being possible for phenyl and benzyl in turn to be mono-    to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₂₁ is hydrogen or C₁-C₈alkyl;-   R₂₂ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN, or-   R₂₂ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₂₁ and R₂₂ together are C₂-C₅alkylene;-   R₂₃ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆Cycloalkyl;-   R₂₄ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₂₅ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₂₆ is hydrogen or C₁-C₈alkyl;-   R₂₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈-alkoxycarbonyl or by —CN, or-   R₂₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₂₆ and R₂₇ together are C₂-C₅alkylene;-   R₂₈ is hydrogen or C₁-C₈alkyl;-   R₂₉ and R₃₀ are each independently of the other hydrogen,    C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono- to    penta-substituted by halogen or mono-, di- or tri-substituted by —CN    or by C₁-C₄alkoxy;-   R₃₁ and R₃₂ are each independently of the other C₁-C₈alkyl,    C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono- to    penta-substituted by halogen or mono-, di- or tri-substituted by —CN    or by C₁-C₄alkoxy;-   m is 0, 1, 2, 3 or 4;-   each R₂ independently is halogen, —CN, —SCN, —OCN, —N₃, —SF₅, —NO₂,    —NR₃₃R₃₄, —CO₂R₃₅, —CONR₃₆R₃₇, —C(R₃₈)═NOR₃₉, —COR₄₀, —OR₄₁, —SR₄₂,    —SOR₄₃, —SO₂R₄₄, —OSO₂R₄₅, —N([CO]_(p)R₄₆)COR₄₇, —N(ORO₅₄)COR₅₅,    —N(R₅₆)SO₂R₅₇, —N(SO₂R₅₈)SO₂R₅₉, —N═C(OR₆₀)R₆₁, —CR₆₂(OR₆₃)OR₆₄,    —OC(O)NR₆₅R₆₆, —SC(O)NR₆₇R₆₈, —OC(S)NR₆₉R₇₀ or —N-phthalimide; or-   R₂ is a 5- to 7-membered heterocyclic ring system which may be    aromatic or partially or fully saturated and may contain from 1 to 4    hetero atoms selected from nitrogen, oxygen and sulfur, it being    possible for that heterocyclic ring system in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy,    C₁-C₄alkoxy-C₁-C₄alkyl, —CN, —NO₂, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl or by C₁-C₆alkylsulfonyl;-   R₃₃ is hydrogen or C₁-C₆alkyl; and-   R₃₄ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    benzyl, it being possible for phenyl and benzyl in turn to be mono-    to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₃₃ and R₃₄ together are a C₂-C₅alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₃₅ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl mono- to penta-substituted    by halogen or mono-, di- or tri-substituted by C₁-C₄alkoxy or by    phenyl, it being possible for phenyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₃₆ is hydrogen or C₁-C₈alkyl;-   R₃₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈-alkoxycarbonyl or by —CN, or-   R₃₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₃₆ and R₃₇ together are C₃-C₅alkylene;-   R₃₈ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₃₉ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₄₀ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₈alkylthio,    —C(O)—C(O)OC₁-C₄alkyl or C₃-C₆-cycloalkyl;-   R₄₁ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₈alkylcarbonyl, C₁-C₈alkoxycarbonyl,    C₃-C₈alkenyloxycarbonyl, C₁-C₆alkoxy-C₁-C₆alkoxycarbonyl,    C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl-C₁-C₆alkyl or    C₁-C₆alkylsulfonyl-C₁-C₆alkyl; or-   R₄₁ is phenyl or phenyl-C₁-C₆alkyl, it being possible for the phenyl    ring in turn to be mono- to penta-substituted by halogen or by    C₁-C₄alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,    C₁-C₄alkoxy, —CN, —NO₂ or by —S(O)₂C₁-C₆alkyl, or-   R₄₁ is C₁-C₈alkyl mono- to penta-substituted by halogen or mono-,    di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl,    C₁-C₆alkylamino, di(C₁-C₆alkyl)amino or by —CN;-   R₄₂ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl mono- to penta-substituted by halogen or mono-, di- or    tri-substituted by —CN or by C₁-C₄alkoxy;-   R₄₃ and R₄₄ are each independently of the other C₁-C₈alkyl,    C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono- to    penta-substituted by halogen or mono-, di- or tri-substituted by —CN    or by C₁-C₄alkoxy;-   R₄₅ is C₁-C₈alkyl, C₁-C₈alkyl mono- to penta-substituted by halogen    or mono-, di- or tri-substituted by —CN or by C₁-C₄alkoxy, or is    C₃-C₈alkenyl or C₃-C₈alkynyl, or-   R₄₅ is phenyl, it being possible for the phenyl ring to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, NO₂,    C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by C₁-C₈alkylsulfonyl;-   R₄₆ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl or    C₁-C₄haloalkyl;-   R₄₇ is hydrogen, C₁-C₈alkyl, C₁-C₄alkoxy, C₃-C₈alkenyl or    C₃-C₈alkynyl, or is C₁-C₈alkyl mono- to penta-substituted by halogen    or mono-, di- or tri-substituted by —CN, C₁-C₄alkoxy,    C₁-C₈alkoxycarbonyl, —NH₂, C₁-C₄alkylamino, di(C₁-C₄alkyl)amino,    —NR₄₈COR₄₉, —NR₅₀SO₂R₅₁, or by —NR₅₂CO₂R₅₃, or-   R₄₇ is phenyl or benzyl, it being possible for phenyl and benzyl in    turn to be mono- to penta-substituted by halogen or by C₁-C₄alkyl or    mono-, di- or tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN,    —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   p is 0 or 1;-   R₄₈, R₄₉, R₅₀, R₅₁, R₅₂ and R₅₃ are each independently of the others    hydrogen, C₁-C₈alkyl, phenyl, benzyl or naphthyl, it being possible    for the three last-mentioned aromatic radicals in turn to be mono-    to penta-substituted by halogen or by C₁-C₈alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄alkylamino,    di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂, C₁-C₄alkylthio,    C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₅₄ and R₅₅ are each independently of the other hydrogen,    C₁-C₈alkyl, or phenyl which may in turn be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by C₁-C₈alkylsulfonyl;-   R₅₆ is hydrogen, C₁-C₈alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    C₃-C₈alkenyl, C₃-C₈alkynyl or benzyl, it being possible for benzyl    in turn to be mono- to penta-substituted by halogen or by C₁-C₄alkyl    or mono-, di- or tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by    C₁-C₈alkylsulfonyl;-   R₅₇ is C₁-C₈alkyl, C₁-C₄haloalkyl, phenyl, benzyl or naphthyl, it    being possible for the last three aromatic rings to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄alkylamino,    di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂, C₁-C₄alkylthio,    C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₅₈ and R₅₉ are each independently of the other C₁-C₈alkyl,    C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl, benzyl or naphthyl, it being    possible for the last three aromatic rings to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄alkylamino,    di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂, C₁-C₄alkylthio,    C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₆₀ and R₆₁ are each independently of the other hydrogen or    C₁-C₆alkyl;-   R₆₂, R₆₃ and R₆₄ are each independently of the others hydrogen or    C₁-C₈alkyl, or-   R₆₃ and R₆₄ together form a C₂-C₅alkylene bridge;-   R₆₅, R₆₆, R₆₇, R₆₈, R₆₉ and R₇₀ are each independently of the others    hydrogen or C₁-C₈alkyl, or-   R₆₅ and R₆₆, or R₆₇ and R₆₈, or R₆₉ and R₇₀ in each case together    form a C₂-C₅alkylene bridge; or-   each R₂ independently is C₁-C₈alkyl, or is C₁-C₈alkyl mono- to    penta-substituted by halogen or mono-, di- or tri-substituted by    —CN, —N₃, —SCN, —NO₂, —NR₇₁R₇₂, —CO₂R₇₃, —CONR₇₄R₇₅, —COR₇₆,    —C(R₇₇)═NOR₇₈, —C(S)NR₇₉R₈₀, —C(C₁-C₄alkylthio)═NR₈₁, —OR₈₂, —SR₈₃,    —SOR₈₄, —SO₂R₈₅, —O(SO₂)R₈₆, —N(R₈₇)CO₂R₈₈, —N(R₈₉)COR₉₀, —S⁺(R₉₁)₂,    —N⁺(R₉₂)₃, —Si(R₉₃)₃ or by C₃-C₆cycloalkyl; or-   each R₂ independently is C₁-C₈alkyl substituted by a 5- to    7-membered heterocyclic ring system which may be aromatic or    partially or fully saturated and may contain from 1 to 4 hetero    atoms selected from oxygen, nitrogen and sulfur, it being possible    for that heterocyclic ring system in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy,    C₁-C₄alkoxy-C₁-C₄alkyl, —CN, —NO₂, C₁-C₆alkylthio,    C₁-C₆alkylsulfinyl or by C₁-C₆alkylsulfonyl; or-   each R₂ independently is C₂-C₈alkenyl, or is C₂-C₈alkenyl mono- to    penta-substituted by halogen or mono-, di- or tri-substituted by    —CN, —NO₂, —CO₂R₉₄, —CONR₉₅R₉₆, —COR₉₇, —C(R₉₈)═NOR₉₉,    —C(S)NR₁₀₀R₁₀₁, —C(C₁-C₄alkylthio)═NR₁₀₂, —OR₁₀₃, —Si(R₁₀₄)₃ or by    C₃-C₆-cycloalkyl; or-   each R₂ independently is C₂-C₈alkynyl, or is C₂-C₈alkynyl mono- to    penta-substituted by halogen or mono-, di- or tri-substituted by    —CN, —CO₂R₁₀₅, —CONR₁₀₆R₁₀₇, —COR₁₀₈, —C(R₁₀₉)═NOR₁₁₀,    —C(S)NR₁₁₁R₁₁₂, —C(C₁-C₄alkylthio)═NR₁₁₃, —OR₁₁₄, —Si(R₁₁₅)₃ or by    C₃-C₆cycloalkyl; or-   each R₂ independently is C₃-C₆cycloalkyl, or is C₃-C₆cycloalkyl    mono- to penta-substituted by halogen or mono-, di- or    tri-substituted by —CN, —CO₂R₁₁₆, —CONR₁₁₇R₁₁₈, —COR₁₁₉,    —C(R₁₂₀)═NOR₁₂₁, —C(S)NR₁₂₂R₁₂₃ or by —C(C₁-C₄alkylthio)═NR₁₂₄; or-   two adjacent R₂ substituents together form a C₁-C₇alkylene bridge    which may be interrupted by from 1 to 3 hetero atoms selected from    oxygen, nitrogen and sulfur and may be mono- to penta-substituted by    halogen or by C₁-C₆alkyl or mono-, di- or tri-substituted by    C₁-C₆alkoxy, the total number of ring atoms being at least 5 and at    most 9; or-   two adjacent R₂ substituents together form a C₂-C₇alkenylene bridge    which may be interrupted by from 1 to 3 hetero atoms selected from    oxygen, nitrogen and sulfur and may be mono- to penta-substituted by    halogen or by C₁-C₆alkyl or mono-, di- or tri-substituted by    C₁-C₆alkoxy, the total number of ring atoms being at least 5 and at    most 9;-   R₇₁ is hydrogen or C₁-C₈alkyl;-   R₇₂ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    benzyl, it being possible for phenyl and benzyl in turn to be mono-    to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₇₁ and R₇₂ together are a C₂-C₅alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₇₃ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl mono- to penta-substituted    by halogen or mono-, di- or tri-substituted by C₁-C₄alkoxy or by    phenyl, it being possible for phenyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₇₄ is hydrogen or C₁-C₈alkyl;-   R₇₅ is hydrogen, C₁-C₈alkyl or C₃-C₇cycloalkyl, or is C₁-C₈alkyl    mono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl,    C₁-C₆alkoxy or by —CN; or-   R₇₅ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₇₄ and R₇₅ together are a C₂-C₅alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₇₆ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₇₇ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₇₈ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl; and-   R₇₉ is hydrogen or C₁-C₈alkyl;-   R₈₀ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈-alkoxycarbonyl or by —CN; or-   R₈₀ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₇₉ and R₈₀ together are C₂-C₅alkylene;-   R₈₁ is hydrogen or C₁-C₈alkyl;-   R₈₂ is —Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl which is mono- to penta-substituted by halogen or mono-,    di- or tri-substituted by —CN, —NH₂, C₁-C₆alkylamino,    di(C₁-C₆alkyl)amino or by C₁-C₄alkoxy;-   R₈₃ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl which is mono- to penta-substituted by halogen or mono-,    di- or tri-substituted by —CN, —NH₂, C₁-C₆alkylamino,    di(C₁-C₆alkyl)amino or by C₁-C₄alkoxy;-   R₈₄, R₈₅ and R₈₆ are each independently of the others C₁-C₈alkyl,    C₃-C₈alkenyl or C₃-C₈-alkynyl, or C₁-C₈alkyl which is mono- to    penta-substituted by halogen or mono-, di- or tri-substituted by —CN    or by C₁-C₄alkoxy;-   R₈₇ and R₈₉ are each independently of the other hydrogen, C₁-C₈alkyl    or C₁-C₈alkoxy;-   R₈₈ is C₁-C₈alkyl;-   R₉₀ is hydrogen or C₁-C₈alkyl;-   R₉₁ is C₁-C₄alkyl;-   R₉₂ and R₉₃ are each independently of the other C₁-C₆alkyl;-   R₉₄ is hydrogen or is C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, each    of which may be mono- to penta-substituted by halogen or mono-, di-    or tri-substituted by C₁-C₄alkoxy or by phenyl, it being possible    for phenyl in turn to be mono- to penta-substituted by halogen or by    C₁-C₄-alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,    C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl;-   R₉₅ is hydrogen or C₁-C₈alkyl;-   R₉₆ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₉₆ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₉₅ and R₉₆ together are C₂-C₅alkylene;-   R₉₇ and R₉₈ are each independently of the other hydrogen,    C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₉₉ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₁₀₀ is hydrogen or C₁-C₈alkyl;-   R₁₀₁ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈-alkoxycarbonyl or by —CN; or-   R₁₀₁ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₁₀₀ and R₁₀₁ together are C₂-C₅alkylene;-   R₁₀₂ is hydrogen or C₁-C₈alkyl;-   R₁₀₃ is hydrogen, C₁-C₈alkyl, —Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or    C₃-C₈alkynyl;-   R₁₀₄ is C₁-C₆alkyl;-   R₁₀₅ is hydrogen or is C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl,    each of which may be mono- to penta-substituted by halogen or mono-,    di- or tri-substituted by C₁-C₄alkoxy or by phenyl, it being    possible for phenyl in turn to be mono- to penta-substituted by    halogen or by C₁-C₄-alkyl or mono-, di- or tri-substituted by    C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,    C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₁₀₆ is hydrogen or C₁-C₈alkyl;-   R₁₀₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN, or-   R₁₀₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₁₀₆ and R₁₀₇ together are C₂-C₅alkylene;-   R₁₀₈ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₀₉ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₁₀ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₁₁₁ is hydrogen or C₁-C₈alkyl;-   R₁₁₂ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₁₁₂ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₁₁₁ and R₁₁₂ together are C₂-C₅alkylene;-   R₁₁₃ is hydrogen or C₁-C₈alkyl;-   R₁₁₄ is hydrogen, C₁-C₈alkyl, —Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or    C₃-C₈alkynyl;-   R₁₁₅ is C₁-C₆alkyl;-   R₁₁₆ is hydrogen or is C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl,    each of which may be mono- to penta-substituted by halogen or mono-,    di- or tri-substituted by C₁-C₄alkoxy or by phenyl, it being    possible for phenyl in turn to be mono- to penta-substituted by    halogen or by C₁-C₄-alkyl or mono-, di- or tri-substituted by    C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,    C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₁₁₇ is hydrogen or C₁-C₈alkyl;-   R₁₁₈ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₁₁₈ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₁₁₇ and R₁₁₈ together are C₂-C₅alkylene;-   R₁₁₉ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₂₀ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₂₁ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₁₂₂ is hydrogen or C₁-C₈alkyl;-   R₁₂₃ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₁₂₃ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono- to    penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- or    tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or-   R₁₂₂ and R₁₂₃ together are C₂-C₅alkylene; and-   R₁₂₄ is hydrogen or C₁-C₈alkyl,-   and to the agrochemically acceptable salts and all stereoisomers and    tautomers of the compounds of formula I.

When n is 0, all free valencies on the heterocyclic groups Q₁ to Q₈ ofthe compounds of formula I are occupied by hydrogen. When m is 0, allfree valencies on the phenyl or pyridyl ring of the compounds of formulaI are occupied by hydrogen.

Examples of substituents that are formed as a result of R₅ and R₆together or R₁₈ and R₁₉ together or R₃₆ and R₃₇ together or R₇₄ and R₇₅together being a C₂-C₅alkylene chain which may be interrupted by anoxygen or sulfur atom are piperidine, morpholine, thiomorpholine andpyrrolidine.

Examples of heterocyclic ring systems which may be aromatic or partiallyor fully saturated in the definition of R₂ are:

The alkyl groups appearing in the substituent definitions may bestraight-chained or branched and are, for example, methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and thepentyl, hexyl, heptyl and octyl isomers.

Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine orchlorine.

Haloalkyl is, for example, fluoromethyl, difluoromethyl,trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl,2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl,1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl or2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl,difluoromethyl, trifuoromethyl or dichlorofluoromethyl.

Alkoxy groups have a chain length of preferably from 1 to 6, especiallyfrom 1 to 4, carbon atoms. Alkoxy is, for example, methoxy, ethoxy,propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, orthe pentyloxy and hexyloxy isomers; preferably methoxy or ethoxy.

Alkoxy, alkenyl, alkynyl, alkoxyalkyl, alkylthio, alkylsulfonyl,alkylsulfinyl, alkylaminoalkoxy, alkoxycarbonyl, alkylcarbonyloxy,alkenylthio, alkenylsulfonyl, alkenylsulfinyl, alkynylsulfonyl,alkynylthio and alkynylsulfinyl groups are derived from the mentionedalkyl groups. The alkenyl and alkynyl groups may be mono- orpoly-unsaturated. Alkenyl is, for example, vinyl, allyl, methallyl,1-methylvinyl or but-2-en-1-yl. Alkynyl is, for example, ethynyl,propargyl, but-2-yn-1-yl, 2-methylbutyn-2-yl or but-3-yn-2-yl.

Alkylthio groups preferably have a chain length of from 1 to 4 carbonatoms. Alkylthio is, for example, methylthio, ethylthio, propylthio,isopropylthio, n-butylthio, isobutylthio, sec-butylthio ortert-butylthio, preferably methylthio or ethylthio. Alkylsulfinyl is,for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl,isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinylor tert-butylsulfinyl; preferably methylsulfinyl or ethylsulfinyl.Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl,propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl,sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl orethylsulfonyl.

Alkoxyalkyl groups preferably have from 1 to 6 carbon atoms. Alkoxyalkylis, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl,n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.

Substituents where two adjacent R₁ substituents (on the group Q₁, Q₂, Q₃or Q₅) together form a C₁-C₇alkylene bridge which may be interrupted byfrom 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur andmay be mono- to penta-substituted by halogen or by C₁-C₆alkyl or mono-,di- or tri-substituted by C₁-C₆alkoxy, the total number of ring atomsbeing at least 5 and at most 9, or where two adjacent R₁ substituentstogether form a C₂-C₇alkenylene bridge which may be interrupted by from1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may bemono- to penta-substituted by halogen or by C₁-C₆alkyl or mono-, di- ortri-substituted by C₁-C₆alkoxy, the total number of ring atoms being atleast 5 and at most 9, have, for example, the following structures:

Substituents where two adjacent R₂ substituents together form aC₁-C₇alkylene bridge which may be interrupted by from 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur and may be mono- topenta-substituted by halogen or by C₁-C₆alkyl or mono-, di- ortri-substituted by C₁-C₆alkoxy, the total number of ring atoms being atleast 5 and at most 9, or where two adjacent R₂ substituents togetherform a C₂-C₇alkenylene bridge which may be interrupted by from 1 to 3hetero atoms selected from oxygen, nitrogen and sulfur and may be mono-to penta-substituted by halogen or by C₁-C₆alkyl or mono-, di- ortri-substituted by C₁-C₆alkoxy, the total number of ring atoms being atleast 5 and at most 9, have, for example, the following structures:

The invention relates also to the salts which the compounds of formula Iare able to form preferably with amines, alkali metal and alkaline earthmetal bases or quaternary ammonium bases. Suitable salt formers aredescribed, for example, in WO 98/41089.

Among the alkali metal and alkaline earth metal hydroxides as saltformers, special mention should be made of the hydroxides of lithium,sodium, potassium, magnesium and calcium, especially the hydroxides ofsodium and potassium.

Examples of amines suitable for ammonium salt formation include ammoniaas well as primary, secondary and tertiary C₁-C₁₈alkylamines,C₁-C₄hydroxyalkylamines and C₂-C₄alkoxyalkylamines, for examplemethylamine, ethylamine, n-propylamine, isopropylamine, the fourbutylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine,octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine,heptadecylamine, octadecylamine, methyl-ethylamine,methyl-isopropylamine, methyl-hexylamine, methyl-nonylamine,methyl-pentadecylamine, methyl-octadecylamine, ethyl-butylamine,ethyl-heptylamine, ethyl-octylamine, hexyl-heptylamine,hexyl-octylamine, dimethylamine, diethylamine, di-n-propylamine,diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine,dihexylamine, diheptylamine, dioctylamine, ethanolamine,n-propanolamine, isopropanolamine, N,N-diethanolamine,N-ethylpropanolamine, N-butylethanolamine, allylamine,n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine,dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine,triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine,triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamineand ethoxyethylamine; hetero-cyclic amines, for example pyridine,quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline,quinuclidine and azepine; primary arylamines, for example anilines,methoxyanilines, ethoxyanilines, o-, m- and p-toluidines,phenylenediamines, benzidines, naphthylamines and o-, m- andp-chloroanilines; but especially triethylamine, isopropylamine anddiisopropylamine.

Preferred quaternary ammonium bases suitable for salt formationcorrespond, for example, to the formula [N(R_(a)R_(b)R_(c)R_(d))]OHwherein R_(a), R_(b), R_(c) and R_(d) are each independently of theothers C₁-C₄alkyl. Other suitable tetraalkylammonium bases with otheranions can be obtained, for example, by anion exchange reactions.

Preference is given to compounds of formula I wherein each R₁independently is halogen, —CN, —SCN, —SF₅, —NO₂, —NR₅R₆, —CO₂R₇,—CONR₈R₉, —C(R₁₀)═NOR₁₁, —COR₁₂, —OR₁₃, —SR₁₄, —SOR₁₅, —SO₂R₁₆,—OSO₂R₁₇, C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl or C₃-C₆cycloalkyl; oris C₁-C₈alkyl, C₂-C₈alkenyl or C₂-C₈alkynyl mono-, di- ortri-substituted by halogen, —CN, —NO₂, —NR₁₈R₁₉, —CO₂R₂₀, —CONR₂₁R₂₂,—COR₂₃, —C(R₂₄)═NOR₂₅, —C(S)NR₂₆R₂₇, —C(C₁-C₄alkylthio)═NR₂₈, —OR₂₉,—SR₃₀, —SOR₃₁, —SO₂R₃₂ or by C₃-C₆cycloalkyl; or

-   each R₁ independently is C₃-C₆cycloalkyl mono-, di- or    tri-substituted by halogen, —CN, —NO₂, —NR₁₈R₁₉, —CO₂R₂₀,    —CONR₂₁R₂₂, —COR₂₃, —C(R₂₄)═NOR₂₅, —C(S)NR₂₆R₂₇,    —C(C₁-C₄alkylthio)═NR₂₈, —SR₃₀, —SOR₃₁, —SO₂R₃₂ or by    C₃-C₆cycloalkyl; or-   each R₁ independently is phenyl which may in turn be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or,-   when Q is a group Q₁, Q₂, Q₃ or Q₅, two adjacent R₁ substituents    together may form a C₁-C₇alkylene bridge which may be interrupted by    from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur    and may be mono-, di- or tri-substituted by halogen, C₁-C₆alkyl or    by C₁-C₆alkoxy, the total number of ring atoms being at least 5 and    at most 9; or,-   when Q is a group Q₁, Q₂, Q₃ or Q₅, two adjacent R₁ substituents    together may form a C₂-C₇alkenylene bridge which may be interrupted    by from 1 to 3 hetero atoms selected from oxygen, nitrogen and    sulfur and may be mono-, di- or tri-substituted by halogen,    C₁-C₆alkyl or by C₁-C₆alkoxy, the total number of ring atoms being    at least 5 and at most 9;-   R₃ or R₄ are each independently of the other hydrogen, halogen, —CN,    C₁-C₄alkyl or C₁-C₄alkoxy; or-   R₃ and R₄ together are C₂-C₅alkylene;-   R₅ is hydrogen or C₁-C₈alkyl;-   R₆ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    bent, it being possible for phenyl and benzyl in turn to be mono-,    di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,    C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₅ and R₆ together are a C₂-C₅alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₇ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl mono-, di- or    tri-substituted by halogen, C₁-C₄alkoxy or by phenyl, it being    possible for phenyl in turn to be mono-, di- or tri-substituted by    halogen, C₁-C₄alkyl, C₁-C₄-haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₈ is hydrogen or C₁-C₈alkyl;-   R₉ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN, or-   R₉ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₈ and R₉ together are C₂-C₅alkylene;-   R₁₀ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₁ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₁₂ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₃ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl; or-   R₁₃ is phenyl or phenyl-C₁-C₆alkyl, it being possible for the phenyl    ring in turn to be mono-, di- or tri-substituted by halogen,    C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₈-alkylthio,    C₁-C₈alkylsulfinyl or by C₁-C₈alkylsulfonyl; or-   R₁₃ is C₁-C₈alkyl mono-, di- or tri-substituted by halogen, —CN,    C₁-C₆alkylamino, di(C₁-C₆-alkyl)amino or by C₁-C₄alkoxy;-   R₁₄ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl mono-, di- or tri-substituted by halogen, —CN or by    C₁-C₄alkoxy;-   R₁₅, R₁₆ and R₁₇ are each independently of the others C₁-C₈alkyl,    C₃-C₈alkenyl or C₃-C₈-alkynyl, or C₁-C₈alkyl mono-, di- or    tri-substituted by halogen, —CN or by C₀-C₄alkoxy;-   R₁₈ is hydrogen or C₁-C₈alkyl;-   R₁₉ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    benzyl, it being possible for phenyl and benzyl in turn to be mono-,    di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,    C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₁₈ and R₁₉ together are a C₂-C₅alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₂₀ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    benzyl, it being possible for phenyl and benzyl in turn to be mono-,    di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,    C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl;-   R₂₁ is hydrogen or C₁-C₈alkyl;-   R₂₂ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN, or-   R₂₂ is C₃-C₈alkenyl, C₃-C₈alkynyl phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₂₁ and R₂₂ together are C₂-C₅alkylene;-   R₂₃ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₂₄ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₂₅ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₂₆ is hydrogen or C₁-C₈alkyl;-   R₂₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN, or-   R₂₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₂₆ and R₂₇ together are C₂-C₅alkylene;-   R₂₈ is hydrogen or C₁-C₈alkyl;-   R₂₉ and R₃₀ are each independently of the other hydrogen,    C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono-, di-    or tri-substituted by halogen, —CN or by C₁-C₄alkoxy;-   R₃₁ and R₃₂ are each independently of the other C₁-C₈alkyl,    C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono-, di- or    tri-substituted by halogen, —CN or by C₁-C₄alkoxy;-   m is 0, 1, 2, 3 or 4;-   each R₂ independently is hydrogen, halogen, —CN, —SCN, —OCN, —N₃,    —SF₅, —NO₂, —NR₃₃R₃₄, —CO₂R₃₅, —CONR₃₆R₃₇, —C(R₃₈)═NOR₃₉, —COR₄₀,    —OR₄₁, —SR₄₂, —SOR₄₃, —SO₂R₄₄, —OSO₂R₄₅, —N([CO]_(p)R₄₆)COR₄₇,    —N(OR₅₄)COR₅₅, —N(R₅₆)SO₂R₅₇, —N(SO₂R₅₈)SO₂R₅₉, —N↑C(OR₆₀)R₆₁,    —CR₆₂(OR₆₃)OR₆₄, —OC(O)NR₆₅R₆₆, —SC(O)NR₆₇R₆₈, —OC(S)NR₆₉R₇₀ or    —N-phthalimide; or-   R₂ is a 5- to 7-membered heterocyclic ring system which may be    aromatic or partially or fully saturated and may contain from 1 to 4    hetero atoms selected from nitrogen, oxygen and sulfur, it being    possible for that heterocyclic ring system in turn to be mono-, di-    or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,    hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkoxy-C₁-C₄alkyl, —CN, —NO₂,    C₁-C₆alkylthio, C₁-C₆alkylsulfinyl or by C₁-C₆alkylsulfonyl;-   R₃₃ is hydrogen or C₁-C₈alkyl; and-   R₃₄ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    benzyl, it being possible for phenyl and benzyl in turn to be mono-,    di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,    C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₃₃ and R₃₄ together are a C₂-C₅alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₃₅ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl mono-, di- or    tri-substituted by halogen, C₁-C₄alkoxy or by phenyl, it being    possible for phenyl in turn to be mono-, di- or tri-substituted by    halogen, C₁-C₄alkyl, C₁-C₄-haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₃₆ is hydrogen or C₁-C₈alkyl;-   R₃₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN, or-   R₃₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₃₆ and R₃₇ together are C₃-C₅alkylene;-   R₃₈ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₃₉ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₈haloalkenyl;-   R₄₀ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₈alkylthio,    —C(O)—C(O)OC₁-C₄alkyl or C₃-C₆cycloalkyl;-   R₄₁ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₈alkylcarbonyl, C₁-C₈alkoxycarbonyl,    C₃-C₈alkenyloxycarbonyl, C₁-C₆alkoxy-C₁-C₆alkoxycarbonyl,    C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl-C₁-C₆alkyl or    C₁-C₆alkylsulfonyl-C₁-C₆alkyl; or-   R₄₁ is phenyl or phenyl-C₁-C₆alkyl, it being possible for the phenyl    ring in turn to be mono-, di- or tri-substituted by halogen,    C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂ or by    —S(O)₂C₁-C₈alkyl, or-   R₄₁ is C₁-C₈alkyl mono-, di- or tri-substituted by —COOH,    C₁-C₈alkoxycarbonyl, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino or by —CN;-   R₄₂ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl mono-, di- or tri-substituted by halogen, —CN or by    C₁-C₄alkoxy;-   R₄₃ and R₄₄ are each independently of the other C₁-C₈alkyl,    C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono-, di- or    tri-substituted by halogen, —CN or by C₁-C₄alkoxy;-   R₄₅ is C₁-C₈alkyl, C₁-C₈alkyl mono-, di- or tri-substituted by    halogen, —ON or by C₁-C₄alkoxy, or is C₃-C₈alkenyl or C₃-C₈alkynyl,    or-   R₄₅ is phenyl, it being possible for the phenyl ring to be mono-,    di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,    C₁-C₄alkoxy, —CN, NO₂, C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by    C₁-C₈alkylsulfonyl;-   R₄₆ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl or    C₁-C₄haloalkyl;-   R₄₇ is hydrogen, C₁-C₈alkyl, C₁-C₄alkoxy, C₃-C₈alkenyl or    C₃-C₈alkynyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by    halogen, —CN, C₁-C₄alkoxy, C₁-C₈alkoxycarbonyl, —NH₂,    C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, —NR₄₈COR₄₉, —NR₅₀SO₂R₅₁ or by    —NR₅₂CO₂R₅₃, or-   R₄₇ is phenyl or benzyl, it being possible for phenyl and benzyl in    turn to be mono-, di- or tri-substituted by halogen, C₁-C₄alkyl,    C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,    C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   p is 0 or 1;-   R₄₈, R₄₉, R₅₀, R₅₁, R₅₂ and R₅₃ are each independently of the others    hydrogen, C₁-C₈alkyl, phenyl, benzyl or naphthyl, it being possible    for the three last-mentioned aromatic radicals in turn to be mono-,    di- or tri-substituted by halogen, C₁-C₈alkyl, C₁-C₄haloalkyl,    C₁-C₄alkoxy, C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₅₄ and R₅₅ are each independently of the other hydrogen,    C₁-C₈alkyl, or phenyl which may in turn be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by    C₁-C₈alkylsulfonyl;-   R₅₆ is hydrogen, C₁-C₈alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    C₃-C₈alkenyl, C₃-C₈alkynyl or benzyl, it being possible for benzyl    in turn to be mono-, di- or tri-substituted by halogen, C₁-C₄alkyl,    C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₈alkylthio,    C₁-C₈alkylsulfinyl or by C₁-C₈alkylsulfonyl;-   R₅₇ is C₁-C₈alkyl, C₁-C₄haloalkyl, phenyl, benzyl or naphthyl, it    being possible for the last three aromatic rings to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₅₈ and R₅₉ are each independently of the other C₁-C₈alkyl,    C₃-C₈alkynyl, C₃-C₈alkynyl, phenyl, benzyl or naphthyl, it being    possible for the last three aromatic rings to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₆₀ and R₆₁ are each independently of the other hydrogen or    C₁-C₆alkyl;-   R₆₂, R₆₃ and R₆₄ are each independently of the others hydrogen or    C₁-C₈alkyl, or-   R₆₃ and R₆₄ together form a C₂-C₅alkylene bridge;-   R₆₅, R₆₆, R₆₇, R₆₈, R₆₉ and R₇₀ are each independently of the others    hydrogen or C₁-C₈alkyl, or-   R₆₅ and R₆₆, or R₆₇ and R₆₈, or R₆₉ and R₇₀ in each case together    form a C₂-C₅alkylene bridge; or-   each R₂ independently is C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by halogen, —CN, —N₃, —SCN, —NO₂, —NR₇₁R₇₂, —CO₂R₇₃,    —CONR₇₄R₇₅, —COR₇₆, —C(R₇₇)═NOR₇₈, —C(S)NR₇₉R₈₀,    —C(C₁-C₄alkylthio)═NR₈₁, —OR₈₂—SR₈₃, —SOR₈₄, —SO₂R₈₅, —O(SO₂)R₈₆,    —N(R₈₇)CO₂R₈₈, —N(R₈₉)COR₉₀, —S⁺(R₉₁)₂, —N⁺(R₉₂)₃, —Si(R₉₃)₃ or by    C₃-C₆cycloalkyl; or-   each R₂ independently is C₁-C₈alkyl substituted by a 5- to    7-membered heterocyclic ring system which may be aromatic or    partially or fully saturated and may contain from 1 to 4 hetero    atoms selected from nitrogen, oxygen and sulfur, it being possible    for that hetero-cyclic ring system in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,    hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkoxy-C₁-C₄alkyl, —CN, —NO₂,    C₁-C₆alkylthio, C₁-C₆alkylsulfinyl or by C₁-C₆alkylsulfonyl; or-   each R₂ independently is C₂-C₈alkenyl, or is C₂-C₈alkenyl mono-, di-    or tri-substituted by —CN, —NO₂, —CO₂R₉₄, —CONR₉₅R₉₆, —COR₉₇,    —C(R₉₈)═NOR₉₉, —C(S)NR₁₀₀R₁₀₁, —C(C₁-C₄alkylthio)═NR₁₀₂, —OR₁₀₃,    —Si(R₁₀₄)₃ or by C₃-C₆cycloalkyl; or-   each R₂ independently is C₂-C₈alkynyl, or is C₂-C₈alkynyl mono-, di-    or tri-substituted by halogen, —CN, —CO₂R₁₀₅, —CONR₁₀₆R₁₀₇, —COR₁₀₈,    —C(R₁₀₉)═NOR₁₁₀, —C(S)NR₁₁₁R₁₁₂, —C(C₁-C₄alkylthio)═NR₁₁₃, —OR₁₁₄,    —Si(R₁₁₅)₃ or by C₃-C₆cycloalkyl; or-   each R₂ independently is C₃-C₆cycloalkyl, or is C₃-C₆cycloalkyl    mono-, di- or tri-substituted by halogen, —CN, —CO₂R₁₁₆,    —CONR₁₁₇R₁₁₈, —COR₁₁₉, —C(R₁₂₀)═NOR₁₂₁, —C(S)NR₁₂₂R₁₂₃ or by    —C(C₁-C₄alkylthio)═NR₁₂₄; or-   two adjacent R₂ substituents together form a C₁-C₇alkylene bridge    which may be interrupted by from 1 to 3 hetero atoms selected from    oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted    by halogen, C₁-C₆alkyl or by C₁-C₆alkoxy, the total number of ring    atoms being at least 5 and at most 9; or-   two adjacent R₂ substituents together form a C₂-C₇alkenylene bridge    which may be interrupted by from 1 to 3 hetero atoms selected from    oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted    by halogen, C₁-C₆alkyl or by C₁-C₆alkoxy, the total number of ring    atoms being at least 5 and at most 9;-   R₇₁ is hydrogen or C₁-C₈alkyl;-   R₇₂ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or    benzyl, it being possible for phenyl and benzyl in turn to be mono-,    di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,    C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₇₁ and R₇₂ together are a C₂-C₅alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₇₃ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl mono-, di- or    tri-substituted by halogen, C₁-C₄alkoxy or by phenyl, it being    possible for phenyl in turn to be mono-, di- or tri-substituted by    halogen, C₁-Q₄alkyl, C₁-C₄-haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,    C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₇₄ is hydrogen or C₁-C₈alkyl;-   R₇₅ is hydrogen, C₁-C₈alkyl or C₃-C₇cycloalkyl, or is C₁-C₈alkyl    mono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl,    C₁-C₆alkoxy or by —CN; or-   R₇₅ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₇₄ and R₇₅ together are a C₂-C₅alkylene chain which may be    interrupted by an oxygen or sulfur atom;-   R₇₆ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₇₇ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₇₈ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl; and-   R₇₉ is hydrogen or C₁-C₈alkyl;-   R₈₀ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₈₀ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₇₉ and R₈₀ together are C₂-C₅alkylene;-   R₈₁ is hydrogen or C₁-C₈alkyl;-   R₈₂ is —Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl which is mono-, di- or tri-substituted by halogen, —CN,    —NH₂, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino or by C₁-C₄alkoxy;-   R₈₃ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is    C₁-C₈alkyl which is mono-, di- or tri-substituted by halogen, —CN,    —NH₂, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino or by C₁-C₄alkoxy;-   R₈₄, R₈₅ and R₈₆ are each independently of the others C₁-C₈alkyl,    C₃-C₈alkenyl or C₃-C₈-alkynyl, or C₁-C₈alkyl which is mono-, di- or    tri-substituted by halogen, —CN or by C₁-C₄-alkoxy;-   R₈₇ and R₈₉ are each independently of the other hydrogen, C₁-C₈alkyl    or C₁-C₈alkoxy;-   R₈₈ is C₁-C₈alkyl;-   R₉₀ is hydrogen or C₁-C₈alkyl;-   R₉₁ is C₁-C₄alkyl;-   R₉₂ and R₉₃ are each independently of the other C₁-C₆alkyl;-   R₉₄ is hydrogen or is C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, each    of which may be mono-, di- or tri-substituted by halogen,    C₁-C₄alkoxy or by phenyl, it being possible for phenyl in turn to be    mono-, di- or tri-substituted by halogen, C₁-C₄alkyl,    C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,    C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₉₅ is hydrogen or C₁-C₈alkyl;-   R₉₆ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₉₆ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₉₅ and R₉₆ together are C₂-C₅alkylene;-   R₉₇ and R₉₈ are each independently of the other hydrogen,    C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₉₉ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₁₀₀ is hydrogen or C₁-C₈alkyl;-   R₁₀₁ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₁₀₁ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₁₀₀ and R₁₀₁ together are C₂-C₅alkylene;-   R₁₀₂ is hydrogen or C₁-C₈alkyl;-   R₁₀₃ is hydrogen, C₁-C₈alkyl, —Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or    C₃-C₈alkynyl;-   R₁₀₄ is C₁-C₆alkyl;-   R₁₀₅ is hydrogen or is C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl,    each of which may be mono-, di- or tri-substituted by halogen,    C₁-C₄alkoxy or by phenyl, it being possible for phenyl in turn to be    mono-, di- or tri-substituted by halogen, C₁-C₄alkyl,    C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,    C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₁₀₆ is hydrogen or C₁-C₈alkyl;-   R₁₀₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN, or-   R₁₀₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₁₀₆ and R₁₀₇ together are C₂-C₅alkylene;-   R₁₀₈ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₀₉ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl,-   R₁₁₀ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₁₁₁ is hydrogen or C₁-C₈alkyl;-   R₁₁₂ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₁₁₂ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₁₁₁ and R₁₁₂ together are C₂-C₅alkylene;-   R₁₁₃ is hydrogen or C₁-C₈alkyl;-   R₁₁₄ is hydrogen, C₁-C₈alkyl, —Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or    C₃-C₈alkynyl;-   R₁₁₅ is C₁-C₆alkyl;-   R₁₁₆ is hydrogen or is C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl,    each of which may be mono-, di- or tri-substituted by halogen,    C₁-C₄alkoxy or by phenyl, it being possible for phenyl in turn to be    mono-, di- or tri-substituted by halogen, C₁-C₄alkyl,    C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,    C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;-   R₁₁₇ is hydrogen or C₁-C₈alkyl;-   R₁₁₈ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₁₁₈ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₁₁₇ and R₁₁₈ together are C₂-C₅alkylene;-   R₁₁₉ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₂₀ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;-   R₁₂₁ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,    C₁-C₄haloalkyl or C₃-C₆haloalkenyl;-   R₁₂₂ is hydrogen or C₁-C₈alkyl;-   R₁₂₃ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or    tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or-   R₁₂₃ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being    possible for phenyl and benzyl in turn to be mono-, di- or    tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,    —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by    C₁-C₄alkylsulfonyl; or-   R₁₂₂ and R₁₂₃ together are C₂-C₅alkylene; and-   R₁₂₄ is hydrogen or C₁-C₈alkyl.

Preference is given also to compounds of formula I wherein each R₁independently is halogen, —CN, —NO₂, —C(R₁₀)═NOR₁₁, —OR₁₃, —SO₂R₁₆,—OSO₂R₁₇, C₁-C₈alkyl or C₂-C₈alkenyl, or is C₁-C₈alkyl mono-, di- ortri-substituted by halogen or by —CN; R₁₀ is hydrogen or C₁-C₄alkyl; andR₁₁ is C₁-C₈alkyl.

Preference is given likewise to compounds of formula I wherein Q is agroup Q₁, Q₂, Q₃ or Q₅. Among those compounds special preference isgiven to those wherein Q is a group Q, or Q₂.

Preference is given furthermore to those compounds of formula I whereineach R₂ independently is halogen, —CN, —SCN, —OCN, —N₃, —CONR₃₆R₃₇,—C(R₃₈)═NOR₃₉, —COR₄₀, —OR₄₁, —OSO₂R₄₅, —N([CO]_(p)R₄₆)COR₄₇,—N(R₅₆)SO₂R₅₇, —N(SO₂R₅₈)SO₂R₅₉, —N═C(OR₆₀)R₆₁ or C₁-C₈alkyl, or isC₁-C₈alkyl mono-, di- or tri-substituted by halogen, —CN, —N₃, —SCN,—CONR₇₄R₇₅, —COR₇₆, —C(R₇₇)═NOR₇₈, —C(S)NR₇₉R₈₀, —OR₈₂, —SOR₈₄, —SO₂R₈₅or by —N(R₈₉)COR₉₀.

The compounds of formula Ia

wherein R₁, R₂, R₃, R₄, Z, m and n are as defined for formula I, can beprepared analogously to known methods described, for example, in“Palladium in Heterocyclic Chemistry” from Tetrahedron Organic ChemistrySeries 52, A Guide for the Synthetic Chemist, Editors Jie Jack Li andGordon W. Gribble, Pergamon 2000, Tetrahedron Lett. 1986 (27), 1171;Tetrahedron Organic Chemistry 2000 (20), 359-362; ibid. 2000 (20),390-394; and K. Sonogashira in Comprehensive Organic, Synthesis, EditorsI. Fleming et al., Oxford 1991, Vol. 3, page 521 ff., for example byreacting a compound of formula IIa

wherein R₁ and n are as defined for formula I (Q=Q₁) and X is halogen,with a compound of formula IIIa

wherein R₃ and R₄ are as defined for formula I and M⁺ is an alkali metalcation such as, for example, a lithium, sodium or potassium cation, toform a compound of formula IVa

wherein R₁, R₃, R₄ and n are as defined for formula I, and then couplingthat compound with a compound of formula V

wherein Z, R₂ and m are as defined for formula I and A is a leavinggroup such as, for example, halogen or trifluoromethanesulfonate, in thepresence of a palladium catalyst.

Preparation of the compounds of formula I wherein Q is a group Q₂, thatis to say compounds of formula Ib

wherein Q is a group Q₃, that is to say compounds of formula Ic

wherein Q is a group Q₄, that is to say compounds of formula Id

wherein Q is a group Q₅, that is to say compounds of formula Ie

and wherein Q is a group Q₆, that is to say compounds of formula If

is carried out in a manner analogous to that described above by way ofexample for the compounds of formula Ia (Q=Q₁).

These preparation procedures for the compounds of formula I areillustrated in Reaction Schemes 1, 2 and 3 specifically using theexample of the compound of formula Ia (Q=Q₁). It is generally true ofall three Reaction Schemes that the various substituents R₁ and R₂ inthe compounds of formulae IIa and V either are already present at theoutset or, however, they may be successively introduced only later inthe reaction sequence, for example by means of nucleophilic orelectrophilic aromatic substitution.

The same is also true of the analogous preparation of compounds offormulae Ib, Ic, Id, le and If (Q is a group Q₂ to Q₆), starting fromthe respective compounds of formulae IIb, IIc, IId, IIe and IIf:

In accordance with Reaction Scheme 1, the compounds of formula Ia can beobtained, for example, by reaction of substituted propargyl ethers offormula IVa with compounds of formula V by means of Sonogashiracoupling.

The propargyl ethers of formula IVa can, for their part, be obtained bya nucleophilic aromatic substitution reaction of compounds of formulaIIa wherein X is halogen with alcoholates of formula IIIa. Suchsubstitution reactions are standard methods and may be carried out, forexample, in analogy to Tetrahedron 1972 (28), 4155; Heterocycles 1990(31), 1275 (for Q=Q₁); J. Org. Chem. 1961 (26), 2764 (for Q=Q₂);Tetrahedron Lett. 1996 (37), 4065; Heterocyclic Chem. 1995 (32), 1057(for Q=Q₃); J. Am. Chem. Soc. 1951 (73), 2986 (for Q=Q₄); Collect Czech.Chem. 1975 (40), 2680 (for Q=Q₅); and Tetrahedron Lett. 1985 (26), 4355(for Q=Q₆).

In the next step, the propargyl ethers of formula IVa are coupled withsubstituted phenyl or pyridine derivatives of formula V (Z is ═N— or═C(R₂)—) under typical Sonogashira conditions (K. Sonogashira inComprehensive Organic Synthesis 1991, Vol. 3, page 521 ff.; J. Org.Chem. 1998 (63), 8551-8553). Suitable catalyst mixtures are, forexample, tetrakis(triphenylphosphine)palladium orbis(triphenylphosphine)palladium(II) dichloride together with copper(I)iodide (CuI); suitable bases are preferably amines, for exampletriethylamine, diethylamine or diisopropylethylamine.

The phenyl or pyridine derivatives of formula V preferably have aleaving group A, A being, for example, halogen ortrifluoromethanesulfonate (Tetrahedron Organic Chemistry 2000 (20),209-213; J. Org. Chem. 1998 (63), 8551-8553) and Tetrahedron Lett. 1986(27), 1171. Solvents used for the Sonogashira reaction are usuallyethers, for example tetrahydrofuran, chlorinated hydrocarbons, forexample chloroform, or dipolar aprotic solvents, for exampledimethylformamide or dimethyl sulfoxide, and also amines, for exampletriethylamine or piperidine.

Pd-catalysed cross-coupling of appropriately substituted phenyl orpyridine derivatives of formula V with propargyl alcohols of formula IIIin accordance with K. Sonogashira, as shown in diagrammatic form inReaction Scheme 2, results in compounds of formula VII. Such reactionsare documented, for example, in Tetrahedron Organic Chemistry 2000 (20),209-213 for pyridine derivatives and in J. Org. Chem. 1988 (53), 386;ibid. 1998 (63), 8551-8553; and Tetrahedron Lett. 1986 (27), 1171 forphenyl derivatives. Subsequent reaction of the propargyl alcohols offormula VII with pyrazine derivatives of formula IIa wherein X ishalogen yields the compounds of formula Ia (Q=Q₁).

The other compounds of formula I wherein Q is a group Q₂, Q₃, Q₄, Q₅ orQ₆ can also be prepared in a manner analogous to that shown in ReactionScheme 2.

The compounds of formula I can also be obtained by further methods suchas, for example, that shown in Reaction Scheme 3.

Activation of the alcohol of formula VII according to Reaction Scheme 3is carried out, for example, by sulfonylation or halogenation.

Sulfonylation of the alcohol of formula VII is a standard reaction andcan be carried out, for example, using a sulfonic acid chloride, forexample mesyl chloride or para-toluenesulfonic acid chloride (p-TosCl),in the presence of a tertiary amine, e.g. triethylamine, or an aromaticamine, e.g. pyridine, in a solvent such as, for example, a chlorinatedhydrocarbon, e.g. carbon tetrachloride or methylene chloride, or anamine, e.g. pyridine. Such reactions are generally known and aredescribed, for example, in J. Org. Chem. 1997 (62), 8987; J. Het. Chem.1995 (32), 875-882; and Tetrahedron Lett. 1997 (38), 8671-8674.Halogenation of the alcohol of formula VII can be carried out in analogyto standard methods. For example, bromination can be successfullycarried out using carbon tetrabromide in the presence oftriphenylphosphine (Synthesis 1998, 1015-1018) in methylene chloride.Chlorination can be successfully carried out using mineral acids, forexample using concentrated hydrochloric acid (J. Org. Chem. 1955 (20),95), or using para-toluenesulfonic acid chloride in the presence of anamine, for example triethylamine, in a solvent, for example methylenechloride (Tetrahedron Lett. 1984 (25), 2295). Preparation of thecompound of formula Ia according to Reaction Scheme 3 can be carried outanalogously to Synthesis 1995, 707-712 and Tetrahedron Lett. 1994 (35),6405-6408, for example by means of copper iodide-catalysedetherification of the hydroxy-pyrazine of formula IIa in the presence ofthe tosylate (X₁=OTs) or mesylate (X₁=OMs) or halide (X₁=halogen) offormula VIII. Suitable solvents are dimethylformamide or acetonitrile;suitable bases are preferably potassium carbonate or1,8-diazabicylo[5.4.0]undec-7-ene (DBU). The etherification can also becarried out in halogenated or aromatic hydrocarbons as solvent, forexample in chloroform or in benzene, in the presence of silver carbonateas base. Such selective O-alkylation reactions in the presence of a ringnitrogen atom are described, for example, in Synth. Commun. 1994 (24),1367 and Heterocycles 1990 (31), 819.

A further method by which the compounds of formula I can be prepared isperformed with the aid of Mitsunobu reaction in a manner analogous tothat described, for example, in Synthesis 1981 (1); Tetrahedron Lett.35, 2819-2822 (1994); and Chem. Letters 1994, 539 (with TMAD reagent asa replacement for the DEAD in the two aforesaid references). Thissynthesis route is illustrated in Reaction Scheme 4 using the example ofthe compounds of formula Ia (pyrazinyloxy-alkyne derivatives).

The following applies to the individual reaction steps according toReaction Schemes 1 to 4: The reactions resulting in the compounds offormula I are advantageously performed in aprotic, inert, organicsolvents. Such solvents are hydrocarbons, such as benzene, toluene,xylene or cyclohexane, chlorinated hydrocarbons, such asdichloromethane, trichloromethane, tetrachloromethane or chlorobenzene,ethers, such as diethyl ether, ethylene glycol dimethyl ether,diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles,such as acetonitrile or propionitrile, amides, such asN,N-dimethylformamide, diethyl-formamide or N-methylpyrrolidinone. Thereaction temperatures are preferably from −20° C. to +120° C. Thereactions are generally slightly exothermic and can usually be carriedout at room temperature. For reducing the reaction time or also forinitiation of the reaction, heating, up to the boiling point of thereaction mixture, may, where appropriate, be carried out for a shorttime. It is also possible for the reaction times to be reduced by addinga few drops of base as reaction catalyst. Suitable bases are especiallytertiary amines, such as trimethylamine, triethylamine, quinuclidine,1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or1,5-diazabicyclo[5.4.0]undec-7-ene. However, there may also be used asbases inorganic bases, such as hydrides, e.g. sodium hydride or calciumhydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide,carbonates, e.g. sodium carbonate or potassium carbonate, or hydrogencarbonates, e.g. potassium hydrogen carbonate or sodium hydrogencarbonate.

The compounds of formula I may, in conventional manner, be isolated byconcentrating and/or evaporating off the solvent and purified byrecrystallising or triturating the solid residue in solvents in whichthey are not readily soluble, such as ethers, aromatic hydrocarbons orchlorinated hydrocarbons.

The starting compounds of formula IIa used in Reaction Schemes 1, 2 and3, and the corresponding starting compounds of formulae IIb, IIc, IId,IIe and IIf for preparation of the compounds of formulae Ib, Ic, Id, Ieand If are for the most part known or they can be prepared in analogy toknown methods as described, for example, in J. Org. Chem. 1997 (62),9112; ibid. 1958 (23), 1522; J. Chem. Soc. 1948, 2191; Bull. Soc. Chim.Fr. 1957, 1009; J. Am. Chem. Soc. 74, 1580-1582 (1952); U.S. Pat. No.5,547,919; J. Chem. Soc. 1960, 4590; J. Org. Chem. 1963 (28), 1682; J.Heterocycl. Chem. 1994 (31), 1177; and ibid 1982 (19), 1061.

The starting compounds of formulae III and IIIa are likewise known andin some cases are commercially available, or they can be prepared inanalogy to known methods.

The compounds of formula V are likewise known and in some cases arecommercially available. Examples of substituted compounds of formula Vwherein Z is ═N— are described, for example, in Tetrahedron OrganicChemistry 20, 209 (2000).

The compounds of formulae IV (and IVa to IVf) and VII are novel. Thepresent invention accordingly relates also to those compounds.

For the use according to the invention of the compounds of formula I, orof compositions comprising them, there come into consideration allmethods of application customary in agriculture, for examplepre-emergence application, post-emergence application and seed dressing,and also various methods and techniques such as, for example, thecontrolled release of active ingredient. For that purpose a solution ofthe active ingredient is applied to mineral granule carriers orpolymerised granules (urea/formaldehyde) and dried. If required, it isalso possible to apply a coating (coated granules), which allows theactive ingredient to be released in metered amounts over a specificperiod of time.

The compounds of formula I may be used as herbicides in their unmodifiedform, that is to say as obtained in the synthesis, but they arepreferably formulated in customary manner together with the adjuvantsconventionally employed in formulation technology, for example intoemulsifiable concentrates, directly sprayable or dilutable solutions,dilute emulsions, wettable powders, soluble powders, dusts, granules ormicrocapsules. Such formulations are described, for example, on pages 9to 13 of WO 97/34485. As with the nature of the compositions, themethods of application, such as spraying, atomising, dusting, wetting,scattering or pouring, are chosen in accordance with the intendedobjectives and the prevailing circumstances.

The formulations, that is to say the compositions, preparations ormixtures comprising the compound (active ingredient) of formula I, or atleast one compound of formula I, and, usually, one or more solid orliquid formulation adjuvants, are prepared in known manner, e.g. byhomogeneously mixing and/or grinding the active ingredient(s) with theformulation adjuvants, for example solvents or solid carriers.Surface-active compounds (surfactants) may also be used in addition inthe preparation of the formulations. Examples of solvents and solidcarriers are given, for example, on page 6 of WO 97/34485.

Depending upon the nature of the compound of formula I to be formulated,suitable surface-active compounds are non-ionic, cationic and/or anionicsurfactants and surfactant mixtures having good emulsifying, dispersingand wetting properties. Examples of suitable anionic, non-ionic andcationic surfactants are listed, for example, on pages 7 and 8 of WO97/34485. In addition, the surfactants conventionally employed informulation technology, which are described, inter alia, in“McCutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp.,Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch”, Carl HanserVerlag, Munich/Vienna, 1981, and M. and J. Ash, “Encyclopedia ofSurfactants”, Vol. 1-11, Chemical Publishing Co., New York, 1980-81, arealso suitable for the preparation of the herbicidal compositionsaccording to the invention.

The herbicidal formulations generally contain from 0.1 to 99% by weight,especially from 0.1 to 95% by weight, of herbicide, from 1 to 99.9% byweight, especially from 5 to 99.8% by weight, of a solid or liquidformulation adjuvant, and from 0 to 25% by weight, especially from 0.1to 25% by weight, of a surfactant. Whereas commercial products willpreferably be formulated as concentrates, the end user will normallyemploy dilute formulations. The compositions may also comprise furtheringredients, such as stabilisers, for example vegetable oils orepoxidised vegetable oils (epoxidised coconut oil, rapeseed oil orsoybean oil), anti-foams, for example silicone oil, preservatives,viscosity regulators, binders, tackifiers, and also fertilisers or otheractive ingredients.

The compounds of formula I are generally applied to the plant or thelocus thereof at rates of application of from 0.001 to 4 kg/ha,especially from 0.005 to 2 kg/ha. The concentration required to achievethe desired effect can be determined by experiment. It is dependent onthe nature of the action, the stage of development of the cultivatedplant and of the weed and on the application (place, time, method) andmay vary within wide limits as a function of those parameters.

The compounds of formula I are distinguished by herbicidal andgrowth-inhibiting properties, allowing them to be used in crops ofuseful plants, especially cereals, cotton, soybeans, sugar beet, sugarcane, plantation crops, rape, maize and rice, and also for non-selectiveweed control. The term “crops” is to be understood as including alsocrops that have been made tolerant to herbicides or classes ofherbicides as a result of conventional methods of breeding or geneticengineering techniques. The weeds to be controlled may be eithermonocotyledonous or dicotyledonous weeds, such as, for example,Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Panicum,Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Euphorbia, Monochoria,Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus,Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea,Chrysanthemum, Galium, Viola and Veronica.

The following Examples further illustrate but do not limit theinvention.

PREPARATION EXAMPLES Example P1 Preparation of2-mercapto-5-methoxy-3H-pyrimidin-4-one (see J. Chem. Soc. 1960, 4590)

A mixture of 9.9 ml (0.1 mol) of methoxyacetic acid methyl ester and 8.1ml (0.1 mol) of ethyl formate is added dropwise to a stirred suspensionof 2.3 g (0.1 mol) of sodium in 30 ml of toluene, the temperature beingkept below 30° C. On the following day, the toluene phase is decantedoff and 15 ml of ethanol and 7.6 g (0.1 mol) of thiourea are added tothe crude, viscous sodium salt of 3-hydroxy-2-methoxyacrylic acid methylester. The resulting mixture is stirred at 20° C. for 1 hour and is thenheated at reflux temperature for 5 hours. After cooling, the solidformed is dissolved in 50 ml of water and the resulting solution isrendered neutral with 6N hydrochloric acid. The desired title compoundprecipitates out and can, after drying at 100° C., be obtained in ayield of 8.3 g (52% of theory). The product can be further used directlyfor further reactions.

For purification, the crude product is recrystallised from water, thedesired title compound being obtained in the form of needles having amelting point of 280-281° C. (decomposition).

¹H NMR (300 MHz, DMSO-d₆): 12.526 ppm (broad singlet, 1H); 12.136 ppm(broad singlet, 1H); 7.016 ppm (s, 1H); 3.630 ppm (s, 3H).

Example P2 Preparation of 5-methoxy-3H-pyrimidin-4-one (see J. Chem.Soc. 1960, 4590)

3.9 g of Raney nickel (slurry) are added to a hot solution of 4.1 g(0.026 mol) of 2-mercapto-5-methoxy-3H-pyrimidin-4-one (Example P1) in60 ml of water. After vigorous stirring for 8 hours at refluxtemperature, the reaction mixture is filtered and the combined filtratesand washing fractions are concentrated by evaporation on a hot waterbath. The residue obtained is recrystallised from ethanol in thepresence of activated carbon. The desired target compound is obtained ina yield of 1.9 g (69% of theory) in the form of needles having a meltingpoint of 206-208° C.

¹H NMR (300 MHz, DMSO-d₆): 7.828 ppm (s, 1H); 7.527 ppm (s, 1H); 3.728ppm (s, 3H).

Example P3 Preparation of 4-chloro-5-methoxy-pyrimidine (see J. Chem.Soc. 1960, 4590 and U.S. Pat. No. 5,547,919)

A suspension of 1.9 g (0.015 mol) of 5-methoxy-3H-pyrimidin-4-one(Example P2) in 4.2 ml (0.046 mol) of phosphorus oxychloride and 5.0 ml(0.031 mol) of N,N-diethylaniline is heated at 115° C. for 3 hours. Thedark, homogeneous mixture obtained is hydrolysed by adding crushed ice,the temperature being kept below 30° C. Extraction with diethyl ether,drying of the combined organic ethereal phases over sodium sulfate, andpurification on a silica gel column (eluant: ethyl acetate/n-hexane 1/9)yields the desired target compound in a yield of 1.3 g (58% of theory).

Further purification by means of sublimation at 80-85° C./15 Torr yieldsthe desired title compound, having a melting point of 63-64° C.

¹H NMR (300 MHz, CDCl₃): 8.635 ppm (s, 1H); 8.321 ppm (s, 1H); 4.025 ppm(s, 3H).

Example P4 Preparation of 5-methoxy-4-prop-2-ynyloxy-pyrimidine

0.59 ml (0.01 mol) of propargyl alcohol is added to a suspension of0.265 g (0.011 mol) of sodium hydride in 8 ml of N,N-dimethylformamidewhilst cooling with ice-water. The reaction mixture is stirred at 20° C.for 30 minutes and then 1.44 g (0.01 mol) of4-chloro-5-methoxy-pyrimidine (Example P3) at 0° C. are added andstirring is carried out at 20° C. for a further 3 hours. The reaction isstopped by adding ethyl acetate and water, and working-up is carriedout. Purification of the resulting crude product on a silica gel column(eluant: ethyl acetate/isohexane 1/3) yields the desired targetcompound, having a melting point of 86-87° C., in a yield of 1.3 g (79%of theory).

¹H NMR (300 MHz, CDCl₃): 8.436 ppm (s, 1H); 8.101 ppm (s, 1H); 5.090 ppm(d, 2H); 3.945 ppm (s, 3H); 2.510 ppm (dxd, 1H).

Example P5 Preparation of{3-[3-(5-methoxy-pyrimidin-4-yloxy)-prop-1-ynyl]-phenyl}-acetonitrile

0.493 g (0.003 mol) of 5-methoxy-4-prop-2-ynyloxy-pyrimidine (ExampleP4) and 1.094 g (0.0045 mol) of 3-iodophenylacetonitrile are dissolvedin separate amounts, each of 4 ml, of piperidine. Then, to the solutionof 3-iodophenylacetonitrile, there are added first 0.175 g (0.00015 mol)of tetrakis(triphenylphosphine)palladium (Pd(PPh₃)₄) and also, after 5minutes, the piperidine solution containing5-methoxy-4-prop-2-ynyloxy-pyrimidine. 0.060 g (0.0003 mol) of copper(I)iodide (CuI) is added to the combined solution, whilst cooling with ice,and the reaction mixture is stirred at 20° C. for 3 hours. Working-up ofthe reaction mixture is starting by adding 25 ml of saturated aqueousammonium chloride solution and 25 ml of ethyl acetate. The aqueous phaseis extracted twice with ethyl acetate, and the combined organic phasesare washed with saturated sodium chloride solution and dried over sodiumsulfate. After filtering and concentrating by evaporation, 1.3 g of ayellow oil are obtained, which is purified by silica gel chromatography(eluant: ethyl acetate/isohexane 1/1). The desired target compound,having a melting point of 96-97° C., is obtained in a yield of 0.75 g(89% of theory).

¹H NMR (300 MHz, CDCl₃): 8.457 ppm (s, 1H); 8.116 ppm (s, 1H);7.282-7.434 ppm (m, 4H); 5.318 ppm (s, 2H); 3.964 ppm (s, 3H); 3.724 ppm(s, 2H).

Example P6 Preparation of 2-methoxy-pyrazine 4-oxide (see J. Org. Chem.1963 (28), 1682)

1.9 g (0.017 mol) of 30% hydrogen peroxide are added to a solution of1.1 g (0.01 mol) of 2-methoxy-pyrazine in 3 ml of glacial acetic acidand the resulting solution is heated at 65-68° C. for 17 hours. Thesolution is concentrated to 1/3 of the original volume, diluted with thesame amount of water and concentrated again. The residue is extractedwith chloroform and the combined organic phases are washed withsaturated sodium chloride solution and dried over sodium sulfate. Afterconcentration, two amounts, each of 25 ml, of toluene are added to theresidue obtained and are concentrated again. The desired title compound,which can be used directly for further reactions, is obtained in a yieldof 0.98 g (77% of theory).

¹H NMR (300 MHz, CDCl₃): 7.988 ppm (d (J=4.2 Hz), 1H); 7.706-7.773 ppm(m, 1H); 7.745 ppm (dxd (J=4.2 and 1.5 Hz), 1H); 3.995 ppm (s, 3H).

Example P7 Preparation of 2-chloro-6-methoxy-pyrazine (see J.Heterocycl. Chem. 1994 (31), 1177)

A mixture of 0.98 g (0.0078 mol) of 2-methoxy-pyrazine 4-oxide (ExampleP6) in 4 ml of phosphoryl chloride is stirred for 2 hours whilst heatingat reflux, with 1.25 ml (0.0078 mol) of N,N-diethylaniline being meteredin with the aid of a syringe before the start of the reaction. Theresulting solution is cooled to 20° C. and poured onto ice-water. Afteradjusting the mixture to pH 9 with 30% aqueous sodium hydroxidesolution, extraction is carried out four times, using 10 ml ofchloroform each time. The combined extracts are washed with 3Nhydrochloric acid and saturated sodium chloride solution and are driedover sodium sulfate. A mixture of the desired target compound and of theisomeric 2-chloro-3-methoxy-pyrazine is obtained, which can be separatedon a silica gel column (eluant: ethyl acetate/isohexane 1/8). Thedesired title compound is obtained in a yield of 0.29 g (25% of theory),and the isomeric 2-chloro-3-methoxy-pyrazine in a yield of 0.38 g (33%of theory).

¹H NMR (300 MHz, CDCl₃) of the title compound: 8.143 ppm (s, 1H); 8.131ppm (s, 1H); 3.988 ppm (s, 3H).

¹H NMR (300 MHz, CDCl₃) of 2-chloro-3-methoxy-pyrazine: 8.031 ppm (d(J=2.7 Hz), 1H); 7.937 ppm (d (J=2.7 Hz), 1H); 4.057 ppm (s, 3H).

Example P8 Preparation of 2-chloro-6-methoxy-pyrazine 4-oxide

To a solution of 0.49 g (0.0034 mol) of 2-chloro-6-methoxy-pyrazine(Example P7) in 9 ml of dichloromethane there are added, under an argongas atmosphere, first, within a period of 45 minutes and at 20° C., 0.19g (0.002 mol) of hydrogen peroxide-urea adduct and then, dropwise, 0.3ml (0.0021 mol) of trifluoroacetic anhydride in dichloromethane. Thenthere are again added, within a period of 45 minutes and at 20° C., 0.19g (0.002 mol) of hydrogen peroxide-urea adduct and 0.3 ml (0.0021 mol)of trifluoroacetic anhydride in dichloromethane, and the reactionmixture is stirred further at 20° C. for 30 minutes. The reaction isstopped by adding water, and the aqueous phase obtained is extractedwith chloroform. The combined organic phases are washed with 5% sodiumhydrogen carbonate solution and saturated sodium chloride solution anddried over sodium sulfate. The desired title compound, having a meltingpoint of 121-123° C., is obtained in a yield of 0.53 g (98% of theory).The compound can be used directly for the next reaction step.

¹H NMR (300 MHz, CDCl₃): 7.802 ppm (d (J=1.2 Hz), 1H); 7.691 ppm (d(J=1.2 Hz), 1H); 4.012 ppm (s, 3H).

Example P9 Preparation of 2,5-dichloro-3-methoxy-pyrazine (see J.Heterocycl. Chem. 1982 (19), 1061)

A mixture of 0.53 g (0.0033 mol) of 2-chloro-6-methoxy-pyrazine 4-oxide(Example P8) and 3 ml of phosphoryl chloride is boiled at reflux for 90minutes. The excess of phosphoryl chloride is then removed under reducedpressure and the reaction mixture is poured onto ice-water and extractedwith chloroform. The organic phase is washed with 5% sodium hydrogencarbonate solution and dried over sodium sulfate. After removal of thesolvent by distillation, the crude product is obtained, which ispurified on a silica gel column (eluant: ethyl acetate/isohexane 1/9).The desired target compound is obtained in a yield of 0.55 g (92% oftheory).

¹H NMR (300 MHz, CDCl₃): 7.953 ppm (s, 1H); 4.078 ppm (s, 3H).

Example P10 Preparation of 5-chloro-3-methoxy-2-prop-2-ynyloxy-pyrazine

0.23 ml (0.0038 mol) of propargyl alcohol is added to a suspension of0.155 g (0.0038 mol) of sodium hydride (60% suspension in oil) in 5 mlof N,N-dimethylformamide, whilst cooling with ice-water, and theresulting mixture is stirred at 20° C. for 30 minutes. Then, 0.55 g(0.003 mol) of 2,5-dichloro-3-methoxy-pyrazine (Example P9) is added,whilst cooling in an ice-water bath, and the mixture is stirred furtherat 20° C. for 3 hours. The reaction is stopped by adding ethyl acetateand water, and the aqueous phase is extracted with ethyl acetate. Thecombined organic phases are washed with saturated sodium chloridesolution and dried over sodium sulfate. The crude product obtained ispurified on a silica gel column (eluant: ethyl acetate/isohexane 1/9).The desired title compound, having a melting point of 71-72° C., isobtained in a yield of 0.23 g (53% of theory), and 0.07 g (17% oftheory) of the isomeric 2-chloro-3-methoxy-5-prop-2-ynyloxy-pyrazine isobtained.

¹H NMR (300 MHz, CDCl₃) of the desired title compound: 7.650, ppm (s,1H); 5.007 ppm (d (J=2.4 Hz), 2H); 4.043 ppm (s, 3H); 2.496 ppm (dxd(J=2.4 Hz), 1H).

¹H NMR (300 MHz, CDCl₃) of the isomeric2-chloro-3-methoxy-5-prop-2-ynyloxy-pyrazine: 7.649 ppm (s, 1H); 4.953ppm (d (J=2.4 Hz), 2H); 4.057 ppm (s, 3H); 2.493 ppm (dxd (J=2.4 Hz),1H).

Example P11 Preparation of{3-[3-(5-chloro-3-methoxy-pyrazin-2-yloxy)-prop-1-ynyl]-phenyl}-acetonitrile

To a solution of 0.33 g (0.0016 mol) of5-chloro-3-methoxy-2-prop-2-ynyloxy-pyrazine (Example P10) and 0.60 g(0.0025 mol) of 3-iodophenylacetonitrile in 3 ml ofN,N-dimethyl-formamide and 1.5 ml of diisopropylethylamine there isadded a mixture of 0.03 g of bis(triphenylphosphine)palladium dichloride(PdCl₂(PPh₃)₂), 0.03 g of triphenylphosphine (PPh₃) and 0.03 g ofcopper(I) iodide (CuI) at 20° C. under an argon gas atmosphere. Thereaction mixture is stirred at 20° C. for 90 minutes. The reaction isstopped by adding ice, and the aqueous phase is extracted three times,using 10 ml of ethyl acetate each time. The combined organic phases arewashed with saturated sodium chloride solution, dried over sodiumsulfate, filtered and concentrated. The crude product obtained ispurified on a silica gel column (eluant: ethyl acetate/isohexane 1/3).0.20 g (38% of theory) of the desired title compound, having a meltingpoint of 99-100° C., is obtained.

¹H NMR (300 MHz, CDCl₃): 7.671 ppm (s, 1H); 7.278-7.425 ppm (m, 4H);5.233 ppm (s, 2H); 4.060 ppm (s, 3H); 3.721 ppm (s, 2H).

It is also possible for the preferred compounds listed in the followingTables to be obtained in a manner analogous to that described inExamples P1 to P11 or by the methods shown in Reaction Schemes 1-4 andin the references indicated. In the column “Phys. data”, the indicatedtemperatures denote the melting point (m.p.) of the compounds inquestion. TABLE 1 Compounds of formula Ia1: (Ia1)

Comp. Phys. data no. R₁ R₂ R₃ R₄ m.p. (° C.) 1.001 3-OCH₃, 5-CN 3-Cl H H1.002 3-F, 5-Cl 3-Cl H H 1.003 3-Cl, 5-Cl 3-Cl H H 1.004 3-OCH₃, 5-F3-Cl H H 1.005 3-OCH₃, 5-Cl 3-Cl H H 1.006 3-OCH₃, 5-Br 3-Cl H H 1.0073-Cl, 5-CF₃ 3-Cl H H 1.008 3-OCH₃, 5-CF₃ 3-Cl H H 1.009 3-OCH₃, 5-CH₃3-Cl H H 1.010 3-OCH₃, 5-CH═NOCH₃ 3-Cl H H 1.011 3-F, 5-CF₃ 3-Cl H H1.012 3-OCH₃ 3-Cl H H 1.013 3-OCH₃, 5-CN 3-CH₂CN, 4-F H H 1.014 3-F,5-Cl 3-CH₂CN, 4-F H H 1.015 3-Cl, 5-Cl 3-CH₂CN, 4-F H H 1.016 3-OCH₃,5-F 3-CH₂CN, 4-F H H 1.017 3-OCH₃, 5-Cl 3-CH₂CN, 4-F H H 1.018 3-OCH₃,5-Br 3-CH₂CN, 4-F H H 1.019 3-Cl, 5-CF₃ 3-CH₂CN, 4-F H H 1.020 3-OH₃,5-CF₃ 3-CH₂CN, 4-F H H 1.021 3-OCH₃, 5-CH₃ 3-CH₂CN, 4-F H H 1.0223-OCH₃, 5-CH═NOCH₃ 3-CH₂CN, 4-F H H 1.023 3-F, 5-CF₃ 3-CH₂CN, 4-F H H1.024 3-OCH₃ 3-CH₂CN, 4-F H H 1.025 3-OCH₃, 5-CN 3-CH(CH₃)CN H H 1.0263-F, 5-Cl 3-CH(CH₃)CN H H 1.027 3-Cl, 5-Cl 3-CH(CH₃)CN H H 1.028 3-OCH₃,5-F 3-CH(CH₃)CN H H 1.029 3-OCH₃, 5-Cl 3-CH(CH₃)CN H H 1.030 3-OCH₃,5-Br 3-CH(CH₃)CN H H 1.031 3-Cl, 5-CF₃ 3-CH(CH₃)CN H H 1.032 3-OCH₃,5-CF₃ 3-CH(CH₃)CN H H 1.033 3-OCH₃, 5-CH₃ 3-CH(CH₃)CN H H 1.034 3-OCH₃,5-CH═NOCH₃ 3-CH(CH₃)CN H H 1.035 3-F, 5-CF₃ 3-CH(CH₃)CN H H 1.036 3-OCH₃3-CH(CH₃)CN H H 1.037 3-OCH₃, 5-CN 3-CH₂CN H H 1.038 3-F, 5-Cl 3-CH₂CN HH 1.039 3-Cl, 5-Cl 3-CH₂CN H H 1.040 3-OCH₃, 5-F 3-CH₂CN H H 1.0413-OCH₃, 5-Cl 3-CH₂CN H H crystalline 1.042 3-OCH₃, 5-Br 3-CH₂CN H H1.043 3-Cl, 5-CF₃ 3-CH₂CN H H 1.044 3-OCH₃, 5-CF₃ 3-CH₂CN H H 1.0453-OCH₃, 5-CH₃ 3-CH₂CN H H 1.046 3-OCH₃, 5-CH═NOCH₃ 3-CH₂CN H H 1.0473-F, 5-CF₃ 3-CH₂CN H H 1.048 3-OCH₃ 3-CH₂CN H H 104-105 1.049 3-OCH₃,5-F 3-CH₂CN CH₃ H 1.050 3-OCH₃, 5-Cl 3-CH₂CN CH₃ H 1.051 3-OCH₃, 5-CF₃3-CH₂CN CH₃ H 1.052 3-OCH₃, 5-Br 3-CH₂CN CH₃ H 1.053 3-Cl, 5-CF₃ 3-CH₂CNCH₃ H 1.054 3-OCH₃, 5-CN 3-CH₂CN CH₃ H 1.055 3-OCH₃, 5-F 3-CHF₂ H H1.056 3-OCH₃, 5-Cl 3-OH F2 H H 1.057 3-OCH₃, 5-CF₃ 3-CHF₂ H H 1.0583-OCH₃, 5-Br 3-CHF₂ H H 1.059 3-Cl, 5-CF₃ 3-CHF₂ H H 1.060 3-OCH₃, 5-CN3-CHF₂ H H 1.061 3-OCH₃, 5-F 3-CH₃ H H 1.062 3-OCH₃, 5-Cl 3-CH₃ H H1.063 3-OCH₃, 5-CF₃ H H 1.064 3-OCH₃, 5-Br 3-CH₃ H H 1.065 3-Cl, 5-CF₃3-CH₃ H H 1.066 3-OCH₃, 5-CN 3-CH₃ H H 1.067 3-OCH₃, 5-F 3-CH₂—CN F F1.068 3-OCH₃, 5-Cl 3-CH₂—CN F F 1.069 3-OCH₃, 5-CF₃ 3-CH₂—CN F F 1.0703-OCH₃, 5-Br 3-CH₂—CN F F 1.071 3-Cl, 5-CF₃ 3-CH₂—CN F F 1.072 3-OCH₃,5-CN 3-CH₂—CN F F 1.073 5-OCH₃, 6-F 3-CH₂—CN H H 1.074 5-OCH₃, 6-Cl3-CH₂—CN H H crystalline 1.075 5-OCH₃, 6-F 3-CH(CH₃)CN H H 1.076 5-OCH₃,6-Cl 3-CH(CH₃)CN H H 1.077 5-OCH₃, 6-Cl 3-CHF₂ H H 1.078 6-OCH₃ 3-CH₂—CNH H 71-72 1.079 5,6-CH═CH—CH═CH— 3-CH₂—CN H H amorphous 1.0805,6-CH═CCl—CH═CH— 3-CH₂—CN H H solid 1.081 5,6-CH═CH—CH═CH—, 3-CH₂—CN HH solid 3-OCH₃ 1.082 5,6-CH═CCl—CH═CH—, 3-CH₂—CN H H crystalline 3-OCH₃1.083 5,6-CH═CCl—CH═CH—, 4-Cl H H crystalline 3-OCH₃ 1.084 5-Cl, 6-OCH₃3-CH₂—CN H H crystalline 1.085 5,6-CH═CH—CCl═CH—, 3-CH₂—CN H Hcrystalline 3-Cl 1.086 5,6-CCl═CH—CH═CH—, 3-CH₂—CN H H crystalline 3-Cl1.087 3-Cl 3-CH₂—CN H H crystalline 1.088 5,6-CH═CCl—CH═CH—, 3-CH₂—CN HH 3-N-piperidyl 1.089 5,6-CH═CH—CH═CH—, 4-Cl H H 3-(2-thienyl) 1.0905,6-CH═CH—CH═CH—, 4-Cl H H 3-phenyl 1.091 3-OCH₃, 5-Cl 3-CH₂CN H H 1.0923-OCH₃, 5-Cl 3-CH(CH₃)CN H H 1.093 3-OCH₃, 5-Cl 3-Cl H H 1.094 3-OCH₃,5-Cl 3-CH₂—CN, 4-F H H 1.095 3-OCH₃, 5-Cl 3-CH(CH₃)CN, 4-F H H 1.0963-OCH₃, 5-Cl 3-CH₂—CN, 6-F H H 1.097 3-OCH₃, 5-Cl 3-CH(CH₃)CN, 6-F H H1.098 3-OCH₃, 5-Cl 3-CH₂—CN, 4-F, 6-F H H 1.099 3-OCH₃, 5-Cl3-CH(CH₃)CN, 4-F, 6-F H H 1.100 3-OCH₃, 5-Cl 3-CH₂—CN, 4-Cl, 6-F H H1.101 3-OCH₃, 5-Cl 3-CH(CH₃)CN, 4-Cl, 6-F H H 1.102 3-OCH₃, 5-Cl 3-Cl,6-F H H 1.103 3-OCH₃, 5-Cl 3-CH₂—CN, 4-CN H H 1.104 3-OCH₃, 5-Cl3-CH₂—CN, 4-CH₃ H H 1.105 3-OCH₃, 5-Cl 3-CH(CH₃)CN, 4-CH₃ H H 1.1063-OCH₃, 5-Cl 3-Br H H 1.107 3-OCH₃, 5-Cl 3-I H H 1.108 3-OCH₃, 5-Cl 3-I,6-F H H 1.109 3-OCH₃, 5-Cl 3-CH₂—CN, 4-NO₂ H H 1.110 3-OCH₃, 5-Cl3-CH₂—CN, 4-NH₂ H H 1.111 3-OCH₃, 5-Cl 3-CHF₂ H H 1.112 3-OCH₃, 5-Cl3-CHF₂, 4-F H H 1.113 3-OCH₃, 5-Cl 3-CHF₂, 6-F H H 1.114 3-OCH₃, 5-Cl3-CHF₂, 4-F, 6-F H H 1.115 3-OCH₃, 5-CH═NOCH₃ 3-CH₂CN H H 1.116 3-OCH₃,5-CH═NOCH₃ 3-CH(CH₃)CN H H 1.117 3-OCH₃, 5-CH═NOCH₃ 3-Cl H H 1.1183-OCH₃, 5-CH═NOCH₃ 3-CH₂—CN, 4-F H H 1.119 3-OCH₃, 5-CH═NOCH₃3-CH(CH₃)CN, 4-F H H 1.120 3-OCH₃, 5-CH═NOCH₃ 3-CH₂—CN, 6-F H H 1.1213-OCH₃, 5-CH═NOCH₃ 3-CH(CH₃)CN, 6-F H H 1.122 3-OCH₃, 5-CH═NOCH₃3-CH₂—CN, 4-F, 6-F H H 1.123 3-OCH₃, 5-CH═NOCH₃ 3-CH(CH₃)CN, 4-F, 6-F HH 1.124 3-OCH₃, 5-CH═NOCH₃ 3-CH₂—CN, 4-Cl, 6-F H H 1.125 3-OCH₃,5-CH═NOCH₃ 3-CH(CH₃)CN, 4-Cl, 6-F H H 1.126 3-OCH₃, 5-CH═NOCH₃ 3-Cl, 6-FH H 1.127 3-OCH₃, 5-CH═NOCH₃ 3-CH₂—CN, 4-CN H H 1.128 3-OCH₃, 5-CH═NOCH₃3-CH₂—CN, 4-CH₃ H H 1.129 3-OCH₃, 5-CH═NOCH₃ 3-CH(CH₃)CN, 4-CH₃ H H1.130 3-OCH₃, 5-CH═NOCH₃ 3-Br H H 1.131 3-OCH₃, 5-CH═NOCH₃ 3-I H H 1.1323-OCH₃, 5-CH═NOCH₃ 3-I, 6-F H H 1.133 3-OCH₃, 5-CH═NOCH₃ 3-CH₂—CN, 4-NO₂H H 1.134 3-OCH₃, 5-CH═NOCH₃ 3-CH₂—CN, 4-NH₂ H H 1.135 3-OCH₃,5-CH═NOCH₃ 3-CHF₂ H H 1.136 3-OCH₃, 5-CH═NOCH₃ 3-CHF₂, 4-F H H 1.1373-OCH₃, 5-CH═NOCH₃ 3-CHF₂, 6-F H H 1.138 3-OCH₃, 5-CH═NOCH₃ 3-CHF₂, 4-F,6-F H H 1.139 3-OCH₃, 5-Cl 3-CHF₂, 4-Cl, 6-F H H 1.140 3-OCH₃, 5-Cl3-CHF₂, 4-CH₃, 6-F H H 1.141 3-OCH₃, 5-Cl 3-CHF₂, 4-CN, 6-F H H 1.1423-OCH₃, 5-CF₃ 3-CH₂CN, 4-Cl, 6-F H H 1.143 3-OCH₃, 5-CF₃ 3-CH₂CN, 4-CH₃,6-F H H 1.144 3-OCH₃, 5-CF₃ 3-CH₂CN, 4-CN, 6-F H H 1.145 3-OCH₃ 3-CH₂CN,6-F H H 1.146 3-OCH₃ 3-CH₂CN, 4-F H H 1.147 3-OCH₃ 3-CHF₂, 6-F H H 1.1483-OCH₃ 3-CHF₂, 4-F H H 1.149 3-OCH₃ 3-CH(CH₃)CN H H 1.150 3-OCH₃3-CH₂CN, 4-F H H 1.151 3-OCH₃ 3-CH(CH₃)CN, 4-F H H 1.152 3-OCH₃ 3-CH₂CN,6-F H H 1.153 3-OCH₃ 3-CH(CH₃)CN, 6-F H H 1.154 3-OCH₃ 3-CH₂CN, 4-F, 6-FH H 1.155 3-OCH₃ 3-CH(CH₃)CN, 4-F, 6-F H H 1.156 3-OCH₃ 3-CH₂CN, 4-Cl,6-F H H 1.157 3-OCH₃ 3-CH(CH₃)CN, 4-Cl, 6-F H H 1.158 3-OCH₃ 3-Cl, 6-F HH 1.159 3-OCH₃ 3-CH₂CN, 4-CN H H 1.160 3-OCH₃ 3-CH₂CN, 4-CH₃ H H 1.1613-OCH₃ 3-OH(CH₃)CN, 4-CH₃ H H 1.162 3-OCH₃ 3-Br H H 1.163 3-OCH₃ 3-I H H1.164 3-OCH₃ 3-I, 6-F H H 1.165 3-OCH₃ 3-CH₂CN, 4-NO₂ H H 1.166 3-OCH₃3-CH₂CN, 4-NH₂ H H 1.167 3-OCH₃ 3-CHF₂ H H 1.168 3-OCH₃ 3-CHF₂, 4-F H H1.169 3-OCH₃ 3-CHF₂, 6-F H H 1.170 3-OCH₃ 3-CHF₂, 4-F, 6-F H H 1.1713-OCH₃, 5-F 3-CH₂CN, 4-F H H 1.172 3-OCH₃, 5-F 3-CH(CH₃)CN, 4-F H H1.173 3-OCH₃, 5-F 3-CH₂CN, 6-F H H 1.174 3-OCH₃, 5-F 3-CH(CH₃)CN, 6-F HH 1.175 3-OCH₃, 5-F 3-CH₂CN, 4-F, 6-F H H 1.176 3-OCH₃, 5-F 3-CH(CH₃)CN,4-F, 6-F H H 1.177 3-OCH₃, 5-F 3-CH₂CN, 4-Cl, 6-F H H 1.178 3-OCH₃, 5-F3-CH(CH₃)CN, 4-Cl, 6-F H H 1.179 3-OCH₃, 5-F 3-CH₂CN, 4-CN H H 1.1803-OCH₃, 5-F 3-CH₂CN, 4-CH₃ H H 1.181 3-OCH₃, 5-F 3-CH(CH₃)CN, 4-CH₃ H H1.182 3-OCH₃, 5-F 3-CH₂CN, 4-NO₂ H H 1.183 3-OCH₃, 5-F 3-CH₂CN, 4-NH₂ HH 1.184 3-OCH₃, 5-F 3-CHF₂, 4-F H H 1.185 3-OCH₃, 5-F 3-CHF₂, 6-F H H1.186 3-OCH₃, 5-F 3-CHF₂, 4-F, 6-F H H

TABLE 2 Compounds of formula Ia3: (Ia3)

Phys. data Comp. m.p. no. R₁ R₂ R₃ R₄ (° C.) 2.001 3-OCH₃, 5-CN 6-CH₃ HH 2.002 3-F, 5-Cl 6-CH₃ H H 2.003 3-Cl, 5-Cl 6-CH₃ H H 2.004 3-OCH₃, 5-F6-CH₃ H H 2.005 3-OCH₃, 5-Cl 6-CH₃ H H 2.006 3-OCH₃, 5-Br 6-CH₃ H H2.007 3-Cl, 5-CF₃ 6-CH₃ H H 2.008 3-OCH₃, 5-CF₃ 6-CH₃ H H 2.009 3-OCH₃,5-CH₃ 6-CH₃ H H 2.010 3-OCH₃, 5-CH═NOCH₃ 6-CH₃ H H 2.011 3-F, 5-CF₃6-CH₃ H H 2.012 3-OCH₃ 6-CH₃ H H 2.013 3-OCH₃, 5-CN 6-Cl H H 2.014 3-F,5-Cl 6-Cl H H 2.015 3-Cl, 5-Cl 6-Cl H H 2.016 3-OCH₃, 5-F 6-Cl H H 2.0173-OCH₃, 5-Cl 6-Cl H H 2.018 3-OCH₃, 5-Br 6-Cl H H 2.019 3-Cl, 5-CF₃ 6-ClH H 2.020 3-OCH₃, 5-CF₃ 6-Cl H H 2.021 3-OCH₃, 5-CH₃ 6-Cl H H 2.0223-OCH₃, 5-CH═NOCH₃ 6-Cl H H 2.023 3-F, 5-CF₃ 6-Cl H H 2.024 3-OCH₃ 6-ClH H 2.025 3-OCH₃, 5-CN 5-CH₂CN H H 2.026 3-F, 5-Cl 5-CH₂CN H H 2.0273-Cl, 5-Cl 5-CH₂CN H H 2.028 3-OCH₃, 5-F 5-CH₂CN H H 2.029 3-OCH₃, 5-Cl5-CH₂CN H H 2.030 3-OCH₃, 5-Br 5-CH₂CN H H 2.031 3-Cl, 5-CF₃ 5-CH₂CN H H2.032 3-OCH₃, 5-CF₃ 5-CH₂CN H H 2.033 3-OCH₃, 5-CH₃ 5-CH₂CN H H 2.0343-OCH₃, 5-CH═NOCH₃ 5-CH₂CN H H 2.035 3-F, 5-CF₃ 5-CH₂CN H H 2.036 3-OCH₃5-CH₂CN H H 2.037 3-OCH₃, 5-CN 5-CH(CH₃)CN H H 2.038 3-F, 5-Cl5-CH(CH₃)CN H H 2.039 3-Cl, 5-Cl 5-CH(CH₃)CN H H 2.040 3-OCH₃, 5-F5-CH(CH₃)CN H H 2.041 3-OCH₃, 5-Cl 5-CH(CH₃)CN H H 2.042 3-OCH₃, 5-Br5-CH(CH₃)CN H H 2.043 3-Cl, 5-CF₃ 5-CH(CH₃)CN H H 2.044 3-OCH₃, 5-CF₃5-CH(CH₃)CN H H 2.045 3-OCH₃, 5-CH₃ 5-CH(CH₃)CN H H 2.046 3-OCH₃,5-CH═NOCH₃ 5-CH(CH₃)CN H H 2.047 3-F, 5-CF₃ 5-CH(CH₃)CN H H 2.048 3-OCH₃5-OH(CH₃)CN H H 2.049 3-OCH₃, 5-F 5-CH₂—CN F F 2.050 3-OCH₃, 5-Cl5-CH₂—CN F F 2.051 3-OCH₃, 5-CF₃ 5-CH₂—CN F F 2.052 3-OCH₃, 5-Br5-CH₂—CN F F 2.053 3-Cl, 5-CF₃ 5-CH₂—CN F F 2.054 3-OCH₃, 5-CN 5-CH₂—CNF F

TABLE 3 Compounds of formula Ia2: (Ia2)

Comp. Phys. data no. R₁ R₂ R₃ R₄ m.p. (° C.) 3.001 3-OCH₃, 5-CN 4-CH₃ HH 3.002 3-F, 5-Cl 4-CH₃ H H 3.003 3-Cl, 5-Cl 4-CH₃ H H 3.004 3-OCH₃, 5-F4-CH₃ H H 3.005 3-OCH₃, 5-Cl 4-CH₃ H H 3.006 3-OCH₃, 5-Br 4-CH₃ H H3.007 3-Cl, 5-CF₃ 4-CH₃ H H 3.008 3-OCH₃, 5-CF₃ 4-CH₃ H H 3.009 3-OCH₃,5-CH₃ 4-CH₃ H H 3.010 3-OCH₃, 5-CH═NOCH₃ 4-CH₃ H H 3.011 3-F, 5-CF₃4-CH₃ H H 3.012 3-OCH₃ 4-CH₃ H H 3.013 3-OCH₃, 5-CN 4-CH₂—CN H H 3.0143-F, 5-Cl 4-CH₂—CN H H 3.015 3-Cl, 5-Cl 4-CH₂—CN H H 3.016 3-OCH₃, 5-F4-CH₂—CN H H 3.017 3-OCH₃, 5-Cl 4-CH₂—CN H H 3.018 3-OCH₃, 5-Br 4-CH₂—CNH H 3.019 3-Cl, 5-CF₃ 4-CH₂—CN H H 3.020 3-OCH₃, 5-CF₃ 4-CH₂—CN H H3.021 3-OCH₃, 5-CH₃ 4-CH₂—CN H H 3.022 3-OCH₃, 5-CH═NOCH₃ 4-CH₂—CN H H3.023 3-F, 5-CF₃ 4-CH₂—CN H H 3.024 3-OCH₃ 4-CH₂—CN H H 3.025 3-OCH₃,5-F 4-CH₂—CN F F 3.026 3-OCH₃, 5-Cl 4-CH₂—CN F F 3.027 3-OCH₃, 5-CF₃4-CH₂—CN F F 3.028 3-OCH₃, 5-Br 4-CH₂—CN F F 3.029 3-Cl, 5-CF₃ 4-CH₂—CNF F 3.030 3-OCH₃, 5-CN 4-CH₂—CN F F 3.031 3-OCH₃, 5-F 4-CHF₂ H H 3.0323-OCH₃, 5-Cl 4-CHF₂ H H 3.033 3-OCH₃, 5-CF₃ 4-CHF₂ H H 3.034 3-OCH₃,5-Br 4-CHF₂ H H 3.035 3-Cl, 5-CF₃ 4-CHF₂ H H 3.036 3-OCH₃, 5-CN 4-CHF₂ HH

TABLE 4 Compounds of formula Ib₅1: (Ib₅1)

Comp. Phys. data no. R₁ R₂ R₃ R₄ m.p. (° C.) 4.001 2-CN; 4-OCH₃3-CH₂—CN, 4-F H H 4.002 2-Cl, 4-F 3-CH₂—CN, 4-F H H 4.003 2-Cl, 4-Cl3-CH₂—CN, 4-F H H 4.004 2-F, 4-OCH₃ 3-CH₂—CN, 4-F H H 4.005 2-Cl, 4-OCH₃3-CH₂—CN, 4-F H H 4.006 2-Br, 4-OCH₃ 3-CH₂—CN, 4-F H H 4.007 2-CF₃, 4-Cl3-CH₂—CN, 4-F H H 4.008 2-CF₃, 4-OCH₃ 3-CH₂—CN, 4-F H H 4.009 2-CH₃,4-OCH₃ 3-CH₂—CN, 4-F H H 4.010 2-CH═NOCH₃, 4-OCH₃ 3-CH₂—CN, 4-F H H4.011 2-CF₃, 4-F 3-CH₂—CN, 4-F H H 4.012 4-OCH₃ 3-CH₂—CN, 4-F H H 4.0132-CN; 4-OCH₃ 3-CH(CH₃)CN H H 4.014 2-Cl, 4-F 3-CH(CH₃)CN H H 4.015 2-Cl,4-Cl 3-CH(CH₃)CN H H 4.016 2-F, 4-OCH₃ 3-CH(CH₃)CN H H 4.017 2-Cl,4-OCH₃ 3-CH(CH₃)CN H H 4.018 2-Br, 4-OCH₃ 3-CH(CH₃)CN H H 4.0192-CF_(3, 4-Cl) 3-CH(CH₃)CN H H 4.020 2-CF₃, 4-OCH₃ 3-CH(CH₃)CN H H 4.0212-CH₃, 4-OCH₃ 3-CH(CH₃)CN H H 4.022 2-CH═NOCH₃, 4-OCH₃ 3-CH(CH₃)CN H H4.023 2-CF₃, 4-F 3-CH(CH₃)CN H H 4.024 4-OCH₃ 3-CH(CH₃)CN H H 4.0252-CN; 4-OCH₃ 3-CH₂—CN H H 4.026 2-Cl, 4-F 3-CH₂—CN H H 4.027 2-Cl, 4-Cl3-CH₂—CN H H 4.028 2-F, 4-OCH₃ 3-CH₂—CN H H 4.029 2-Cl, 4-OCH₃ 3-CH₂—CNH H crystalline 4.030 2-Br, 4-OCH₃ 3-CH₂—CN H H 4.031 2-CF₃, 4-Cl3-CH₂—CN H H 4.032 2-CF₃, 4-OCH₃ 3-CH₂—CN H H resin 4.033 2-CH₃, 4-OCH₃3-CH₂—CN H H crystalline 4.034 2-CH═NOCH₃, 4-OCH₃ 3-CH₂—CN H H 4.0352-CF₃, 4-F 3-CH₂—CN H H 4.036 4-OCH₃ 3-CH₂—CN H H 4.037 2-F, 4-OCH₃3-CH₂—CN F F 4.038 2-Cl, 4-OCH₃ 3-CH₂—CN F F 4.039 2-CF₃, 4-OCH₃3-CH₂—CN F F 4.040 2-Br, 4-OCH₃ 3-CH₂—CN F F 4.041 2-CF₃, 4-Cl 3-CH₂—CNF F 4.042 2-CN; 4-OCH₃ 3-CH₂—CN F F 4.043 2-NH₂, 4-OCH₃ 3-CH₂—CN H Hcrystalline 4.044 2-SCH₃ 3-CH₂—CN H H 97-98 4.045 2-CF₃, 4-N(CH₃)₂3-CH₂—CN H H crystalline 4.046 2-CH₃, 4-SCH₃ 3-CH₂—CN H H 4.0472-S(O)₂CH₃ 4-Cl H H 4.048 2-CN; 4-OCH₃ 3-CH₂—CN, 6-F H H 4.049 2-Cl, 4-F3-CH₂—CN, 6-F H H 4.050 2-Cl, 4-Cl 3-CH₂—CN, 6-F H H 4.051 2-F, 4-OCH₃3-CH₂—CN, 6-F H H 4.052 2-Cl, 4-OCH₃ 3-CH₂—CN, 6-F H H 4.053 2-Br,4-OCH₃ 3-CH₂—CN, 6-F H H 4.054 2-CF₃, 4-Cl 3-CH₂—CN, 6-F H H 4.0552-CF₃, 4-OCH₃ 3-CH₂—CN, 6-F H H 4.056 2-CH₃, 4-OCH₃ 3-CH₂—CN, 6-F H H4.057 2-CH═NOCH₃, 4-OCH₃ 3-CH₂—CN, 6-F H H 4.058 2-CF₃, 4-F 3-CH₂—CN,6-F H H 4.059 4-OCH₃ 3-CH₂—CN, 6-F H H 4.060 2-CN; 4-OCH₃ 3-CH(CH₃)CN,4-F H H 4.061 2-Cl, 4-F 3-CH(CH₃)CN, 4-F H H 4.062 2-Cl, 4-Cl3-CH(CH₃)CN, 4-F H H 4.063 2-F, 4-OCH₃ 3-CH(CH₃)CN, 4-F H H 4.064 2-Cl,4-OCH₃ 3-CH(CH₃)CN, 4-F H H 4.065 2-Br, 4-OCH₃ 3-CH(CH₃)CN, 4-F H H4.066 2-CF₃, 4-Cl 3-CH(CH₃)CN, 4-F H H 4.067 2-CF₃, 4-OCH₃ 3-CH(CH₃)CN,4-F H H 4.068 2-CH₃, 4-OCH₃ 3-CH(CH₃)CN, 4-F H H 4.069 2-CH═NOCH₃,4-OCH₃ 3-CH(CH₃)CN, 4-F H H 4.070 2-CF₃, 4-F 3-CH(CH₃)CN, 4-F H H 4.0714-OCH₃ 3-CH(CH₃)CN, 4-F H H 4.072 2-CN; 4-OCH₃ 3-CH₂—CN, 4-Cl, 6-F H H4.073 2-Cl, 4-F 3-CH₂—CN, 4-Cl, 6-F H H 4.074 2-Cl, 4-Cl 3-CH₂—CN, 4-Cl,6-F H H 4.075 2-F, 4-OCH₃ 3-CH₂—CN, 4-Cl, 6-F H H 4.076 2-Cl, 4-OCH₃3-CH₂—CN, 4-Cl, 6-F H H 4.077 2-Br, 4-OCH₃ 3-CH₂—CN, 4-Cl, 6-F H H 4.0782-CF₃, 4-Cl 3-CH₂—CN, 4-Cl, 6-F H H 4.079 2-CF₃, 4-OCH₃ 3-CH₂—CN, 4-Cl,6-F H H 4.080 2-CH₃, 4-OCH₃ 3-CH₂—CN, 4-Cl, 6-F H H 4.081 2-CH═NOCH₃,4-OCH₃ 3-CH₂—CN, 4-Cl, 6-F H H 4.082 2-CF₃, 4-F 3-CH₂-CN, 4-Cl, 6-F H H4.083 4-OCH₃ 3-CH₂—CN, 4-Cl, 6-F H H 4.084 2-NH₂, 4-OCH₃ 3-CH(CH₃)CN,4-F H H 4.085 2-SCH₃ 3-CH(CH₃)CN, 4-F H H 4.086 2-CF₃, 4-N(CH₃)₂3-CH(CH₃)CN, 4-F H H 4.087 2-CH₃, 4-SCH₃ 3-CH(CH₃)CN, 4-F H H 4.0882-S(O)₂CH₃ 3-CH(CH₃)CN, 4-F H H 4.089 2-NH₂, 4-OCH₃ 3-CH₂—CN, 6-F H H4.090 2-SCH₃ 3-CH₂—CN, 6-F H H 4.091 2-CF₃, 4-N(CH₃)₂ 3-CH₂—CN, 6-F H H4.092 2-CH₃, 4-SCH₃ 3-CH₂—CN, 6-F H H 4.093 2-S(O)₂CH₃ 3-CH₂—CN, 6-F H H4.094 2-NH₂, 4-OCH₃ 3-CH₂—CN, 4-Cl, 6-F H H 4.095 2-SCH₃ 3-CH₂—CN, 4-Cl,6-F H H 4.096 2-CF₃, 4-N(CH₃)₂ 3-CH₂—CN, 4-Cl, 6-F H H 4.097 2-CH₃,4-SCH₃ 3-CH₂—CN, 4-Cl, 6-F H H 4.098 2-S(O)₂CH₃ 3-CH₂—CN, 4-Cl, 6-F H H4.099 4-OCH₃ 3-CHF₂, 4-F H H 4.100 4-OCH₃ 3-CHF₂, 6-F H H 4.101 4-OCH₃3-CHF₂, 4-F, 6-F H H 4.102 4-OCH₃ 3-CHF₂, 4-Cl, 6-F H H 4.103 4-OCH₃3-CHF₂ H H 4.104 2-Cl, 4-OCH₃ 3-CHF₂, 4-F H H 4.105 2-Cl, 4-OCH₃ 3-CHF₂,6-F H H 4.106 2-01, 4-OCH₃ 3-CHF₂, 4-F, 6-F H H 4.107 2-Cl, 4-OCH₃3-CHF₂, 4-Cl, 6-F H H 4.108 2-Cl, 4-OCH₃ 3-CHF₂ H H 4.109 2-CH₃, 4-OCH₃3-CHF₂, 4-F H H 4.110 2-CH₃, 4-OCH₃ 3-CHF₂, 6-F H H 4.111 2-CH₃, 4-OCH₃3-CHF₂, 4-F, 6-F H H 4.112 2-CH₃, 4-OCH₃ 3-CHF₂, 4-Cl, 6-F H H 4.1132-CH₃, 4-OCH₃ 3-CHF₂ H H 4.114 2-CF₃, 4-OCH₃ 3-CHF₂, 4-F H H 4.1152-CF₃, 4-OCH₃ 3-CHF₂, 6-F H H 4.116 2-CF₃, 4-OCH₃ 3-CHF₂, 4-F, 6-F H H4.117 2-CF₃, 4-OCH₃ 3-CHF₂, 4-Cl, 6-F H H 4.118 2-CF₃, 4-OCH₃ 3-CHF₂ H H4.119 2-CH₃, 4-OCH₃ 3-CHF₂, 4-F H H 4.120 4-OCH₃ 3-CHF₂, 4-F H H 4.1214-OCH₃ 3-CHF₂, 6-F H H 4.122 4-OCH₃ 3-CHF₂, 4-F, 6-F H H 4.123 4-OCH₃3-CHF₂, 4-Cl, 6-F H H 4.124 4-OCH₃ 3-CHF₂ H H

TABLE 5 Compounds of formula Ib₄1: (Ib₄1)

Comp. Phys. data no. R₁ R₂ R₃ R₄ m.p. (° C.) 5.001 2-F, 5-OCH₃ 3-CH₂—CN,4-F H H 5.002 2-Cl, 5-OCH₃ 3-CH₂—CN, 4-F H H 5.003 5-OCH₃ 3-CH₂—CN, 4-FH H 5.004 5-F 3-CH₂—CN, 4-F H H 5.005 5-Cl 3-CH₂—CN, 4-F H H 5.0062-CH₃, 5-Cl 3-CH₂—CN, 4-F H H 5.007 2-F, 5-Cl 3-CH₂—CN, 4-F H H 5.0085-CH₃ 3-CH₂—CN, 4-F H H 5.009 2-F, 5-OCH₃ 3-Cl H H 5.010 2-Cl, 5-OCH₃3-Cl H H 5.011 5-OCH₃ 3-Cl H H 5.012 5-F 3-Cl H H 5.013 5-Cl 3-Cl H H5.014 2-CH₃, 5-Cl 3-Cl H H 5.015 2-Cl, 5-F 3-Cl H H  99-100 5.016 5-CH₃3-Cl H H 5.017 2-F, 5-OCH₃ 3-CH₂—CN H H 5.018 2-Cl, 5-OCH₃ 3-CH₂—CN H H5.019 5-OCH₃ 3-CH₂—CN H H 5.020 5-F 3-CH₂—CN H H 5.021 5-Cl 3-CH₂—CN H H5.022 2-CH₃, 5-Cl 3-CH₂—CN H H crystalline 5.023 2-Cl, 5-F 3-CH₂—CN H H5.024 5-CH₃ 3-CH₂—CN H H 5.025 5-OCH₃ 3-CH₂—CN H H 96-97 5.026 2-CH₃,5-OCH₃ 3-CH₂—CN H H 109-110 5.027 5-OCH₃ 3-CH₂CN, 4-Cl H H 5.028 5-OCH₃3-CH₂CN, 4-CH₃ H H 5.029 5-OCH₃ 3-CH₂CN, 4-F, 6-F H H 5.030 5-OCH₃3-CH₂CN, 4-Cl, 6-F H H 5.031 5-OCH₃ 3-CH₂CN, 4-CH₃, H H 6-F 5.032 5-OCH₃3-CHF₂ H H 5.033 5-OCH₃ 3-CHF₂, 4-F H H 5.034 5-OCH₃ 3-CHF₂, 4-Cl H H5.035 5-OCH₃ 3-CHF₂, 4-CH₃ H H 5.036 5-OCH₃ 3-CHF₂, 4-F, 6-F H H 5.0375-OCH₃ 3-CHF₂, 4-Cl, 6-F H H 5.038 5-OCH₃ 3-CHF₂, 4-CH₃, 6-F H H 5.0395-OCH₃ 3-CH(CH)₃CN H H 5.040 5-OCH₃ 3-CH(CH)₃CN, 4-F H H 5.041 5-OCH₃3-CH(CH)₃CN, 4-Cl H H 5.042 5-OCH₃ 3-CH(CH)₃CN, H H 4-CH₃ 5.043 5-OCH₃3-CH(CH)₃CN, 4-F, H H 6-F 5.044 5-OCH₃ 3-CH(CH)₃CN, 4-Cl, H H 6-F 5.0455-OCH₃ 3-CH(CH)₃CN, H H 4-CH₃, 6-F 5.046 5-OCH₃, 2-CH₃ 3-CH₂CN, 4-F H H5.047 5-OCH₃, 2-CH₃ 3-CH₂CN, 4-Cl H H 5.048 5-OCH₃, 2-CH₃ 3-CH₂CN, 4-CH₃H H 5.049 5-OCH₃, 2-CH₃ 3-CH₂CN, 4-F, 6-F H H 5.050 5-OCH₃, 2-CH₃3-CH₂CN, 4-Cl, 6-F H H 5.051 5-OCH₃, 2-CH₃ 3-CH₂CN, 4-CH₃, H H 6-F 5.0525-OCH₃, 2-F 3-CH₂CN, 4-F H H 5.053 5-OCH₃, 2-F 3-CH₂CN, 4-Cl H H 5.0545-OCH₃, 2-F 3-CH₂CN, 4-CH₃ H H 5.055 5-OCH₃, 2-F 3-CH₂CN, 4-F, 6-F H H5.056 5-OCH₃, 2-F 3-CH₂CN, 4-Cl, 6-F H H 5.057 5-OCH₃, 2-F 3-CH₂CN,4-CH₃, H H 6-F 5.058 2-OCH₂CH₂CH₃, 3-CH₂CN H H resin 6-OCH₃ 5.059 2-CH₃,6-N-piperidyl 3-CH₂CN H H resin 5.060 2-CF₃, 5-OCH₃ 3-CH₂CN H Hcrystalline 5.061 2-SCH₃, 6-OCH₃ 3-CH₂CN H H amorphous 5.062 2-CH₃, 6-Cl3-CH₂CN H H amorphous 5.063 2-SCH₃, 5-OCH₃ 3-CH₂CN H H 87-88 5.0642-CH(CH₃)₂, 3-CH₂CN H H resin 6-CH₂OCH₂CH₃ 5.065 5-NH₂, 6-Cl 3-CH₂CN H Hoil

TABLE 6 Compounds of formula Ib₅3: (Ib₅3)

Comp. Phys. data no. R₁ R₂ R₃ R₄ m.p. (° C.) 6.001 2-CN; 4-OCH₃ 5-CH₂—CNH H 6.002 2-Cl, 4-F 5-CH₂—CN H H 6.003 2-Cl, 4-Cl 5-CH₂—CN H H 6.0042-F, 4-OCH₃ 5-CH₂—CN H H 6.005 2-Cl, 4-OCH₃ 5-CH₂—CN H H 6.006 2-Br,4-OCH₃ 5-CH₂—CN H H 6.007 2-CF₃, 4-Cl 5-CH₂—CN H H 6.008 2-CF₃, 4-OCH₃5-CH₂—CN H H 6.009 2-CH₃, 4-OCH₃ 5-CH₂—CN H H 6.010 2-CH═NOCH₃, 4-OCH₃5-CH₂—CN H H 6.011 2-CF₃, 4-F 5-CH₂—CN H H 6.012 4-OCH₃ 5-CH₂—CN H H6.013 2-CN; 4-OCH₃ 6-Cl H H 6.014 2-Cl, 4-F 6-Cl H H 6.015 2-Cl, 4-Cl6-Cl H H 6.016 2-F, 4-OCH₃ 6-Cl H H 6.017 2-Cl, 4-OCH₃ 6-Cl H H 6.0182-Br, 4-OCH₃ 6-Cl H H 6.019 2-CF₃, 4-Cl 6-Cl H H 6.020 2-CF₃, 4-OCH₃6-Cl H H 6.021 2-CH₃, 4-OCH₃ 6-Cl H H 6.022 2-CH═NOCH₃, 4-OCH₃ 6-Cl H H6.023 2-CF₃, 4-F 6-Cl H H 6.024 4-OCH₃ 6-Cl H H 6.025 4-OCH₃ 6-Cl F F6.026 2-CN, 4-OCH₃ 6-CH₃ H H 6.027 2-Cl, 4-F 6-CH₃ H H 6.028 2-Cl, 4-Cl6-CH₃ H H 6.029 2-F, 4-OCH₃ 6-CH₃ H H 6.030 2-Cl, 4-OCH₃ 6-CH₃ H H 6.0312-Br, 4-OCH₃ 6-CH₃ H H 6.032 2-CF₃, 4-Cl 6-CH₃ H H 6.033 2-CF₃, 4-OCH₃6-CH₃ H H 6.034 2-CH₃, 4-OCH₃ 6-CH₃ H H 6.035 2-CH═NOCH₃, 4-OCH₃ 6-CH₃ HH 6.036 2-CF₃, 4-F 6-CH₃ H H 6.037 4-OCH₃ 6-CH₃ H H 6.038 4-OCH₃ 6-CH₃ FF

TABLE 7 Compounds of formula Ib₂1: (Ib₂1)

Phys. data Comp. m.p. no. R₁ R₂ R₃ R₄ (° C.) 7.001 5-Br 3-Cl H H 7.0025-Cl 3-Cl H H 7.003 5-F 3-Cl H H 7.004 4-CH₃, 6-CH₃ 3-Cl H H 7.0054-CF₃, 6-CF₃ 3-Cl H H 7.006 5-Br 3-CH₂—CN H H solid 7.007 5-Cl 3-CH₂—CNH H 7.008 5-F 3-CH₂—CN H H 95-96 7.009 4-CH₃, 6-CH₃ 3-CH₂—CN H H 7.0104-CF₃, 6-CF₃ 3-CH₂—CN H H 7.011 5-Br 3-CH₂—CN F F 7.012 5-Br 3-CH₂—CN,4-F H H 7.013 5-Br 3-CH(CH₃)CN H H 7.014 H 3-CH₂—CN H H 98 7.015 H 3-ClH H oil 7.016 5-Br 3-Cl H H 132- 133 7.017 5-Br 3-Br H H 142- 143 7.018H 3,4-OCF₂O— H H 94-95 7.019 4-CF₃ 3-CH₂CN H H resin 7.020 5-Cl3-CH₂—CN, 4-Cl, 6-F H H 152- 154 7.021 5-Cl 3-CH₂—CN H H 116- 118 7.0225-Cl 3-CH₂—CN, 4-F H H solid 7.023 5-F 3-CH₂—CN, 6-F H H 96-97 7.0245-CH₂CH₂CH₃ 3-CH₂—CN H H resin 7.025 4-OC₂H₅, 6-OC₂H₅ 3-CH₂—CN H H oil7.026 5-F 3-CH₂—CN, 4-Cl, 6-F H H 163- 164 7.027 5-F 3-CH₂—CN, 4-F H Hsolid 7.028 5-Cl 3-CH₂—CN, 6-F H H 108- 110 7.029 5-Br 3-OCH₂COOCH₃ H H95-97 7.030 5-Cl 3-OCH₂COOCH₃ H H 90-91 7.031 5-Cl 3-CH₂—CN, 4-F, 6-F HH oil 7.032 5-Cl 3-CH₂—CN, 4-NO₂ H H 106- 109 7.033 5-CF₃ 3-CH₂CN H H7.034 5-CF₃ 3-CH(CH₃)CN H H 7.035 5-CF₃ 3-Cl H H 7.036 5-CF₃ 3-CH₂—CN,4-F H H 7.037 5-CF₃ 3-CH(CH₃)CN, 4-F H H 7.038 5-CF₃ 3-CH₂—CN, 6-F H H7.039 5-CF₃ 3-CH(CH₃)CN, 6-F H H 7.040 5-CF₃ 3-CH₂—CN, 4-F, 6-F H H7.041 5-CF₃ 3-CH(CH₃)CN, 4-F, H H 6-F 7.042 5-CF₃ 3-CH₂—CN, 4-Cl, 5-F HH 7.043 5-CF₃ 3-CH(CH₃)CN, 4-Cl, H H 5-F 7.044 5-CF₃ 3-Cl, 6-F H H 7.0455-CF₃ 3-CH₂—CN, 4-CN H H 7.046 5-CF₃ 3-CH₂—CN, 4-CH₃ H H 7.047 5-CF₃3-CH(CH₃)CN, H H 4-CH₃ 7.048 5-CF₃ 3-Br H H 7.049 5-CF₃ 3-I H H 7.0505-CF₃ 3-I, 6-F H H 7.051 5-CF₃ 3-CH₂—CN, 4-NO₂ H H 7.052 5-CF₃ 3-CH₂—CN,4-NH₂ H H 7.053 5-CF₃ 3-CHF₂ H H 7.054 5-CF₃ 3-CHF₂, 4-F H H 7.055 5-CF₃3-CHF₂, 6-F H H 7.056 5-CF₃ 3-CHF₂, 4-F, 6-F H H 7.057 5-Br 3-CH₂CN H H7.058 5-Br 3-CH(CH₃)CN H H 7.059 5-Br 3-Cl H H 132- 133 7.060 5-Br3-CH₂—CN, 4-F H H 7.061 5-Br 3-CH(CH₃)CN, 4-F H H 7.062 5-Br 3-CH₂—CN,6-F H H 7.063 5-Br 3-CH(CH₃)CN, 6-F H H 7.064 5-Br 3-CH₂—CN, 4-F, 6-F HH 7.065 5-Br 3-CH(CH₃)CN, 4-F, H H 6-F 7.066 5-Br 3-CH₂—CN, 4-Cl, 5-F HH 7.067 5-Br 3-CH(CH₃)CN, 4-Cl, H H 5-F 7.068 5-Br 3-Cl, 6-F H H 7.0695-Br 3-CH₂—CN, 4-CN H H 7.070 5-Br 3-CH₂—CN, 4-CH₃ H H 7.071 5-Br3-CH(CH₃)CN, H H 4-CH₃ 7.072 5-Br 3-Br H H 7.073 5-Br 3-I H H 7.074 5-Br3-I, 6-F H H 7.075 5-Br 3-CH₂—CN, 4-NO₂ H H 7.076 5-Br 3-CH₂-CN, 4-NH₂ HH 7.077 5-Br 3-CHF₂ H H 7.078 5-Br 3-CHF₂, 4-F H H 7.079 5-Br 3-CHF₂,6-F H H 7.080 5-Br 3-CHF₂, 4-F, 6-F H H 7.081 5-Cl 3-CH₂CN H H 7.0825-Cl 3-CH(CH₃)CN H H 7.083 5-Cl 3-Cl H H 7.084 5-Cl 3-CH₂—CN, 4-F H H7.085 5-Cl 3-CH(CH₃)CN, 4-F H H 7.086 5-Cl 3-CH₂—CN, 6-F H H 7.087 5-Cl3-CH(CH₃)CN, 6-F H H 7.088 5-Cl 3-CH₂—CN, 4-F, 6-F H H 7.089 5-Cl3-CH(CH₃)CN, 4-F, H H 6-F 7.090 5-Cl 3-CH₂—CN, 4-Cl, 5-F H H 7.091 5-Cl3-CH(CH₃)CN, 4-Cl, H H 5-F 7.092 5-Cl 3-Cl, 6-F H H 7.093 5-Cl 3-CH₂—CN,4-ON H H 7.094 5-Cl 3-CH₂—CN, 4-CH₃ H H 7.095 5-Cl 3-OH(CH₃)CN, H H4-CH₃ 7.096 5-Cl 3-Br H H 7.097 5-Cl 3-I H H 7.098 5-Cl 3-I, 6-F H H7.099 5-Cl 3-CH₂—CN, 4-NO₂ H H 7.100 5-Cl 3-CH₂—CN, 4-NH₂ H H 7.101 5-Cl3-CHF₂ H H 7.102 5-Cl 3-CHF₂, 4-F H H 7.103 5-Cl 3-CHF₂, 6-F H H 7.1045-Cl 3-CHF₂, 4-F, 6-F H H 7.105 5-F 3-CH₂CN H H 7.106 5-F 3-CH(CH₃)CN HH 7.107 5-F 3-Cl H H 7.108 5-F 3-CH₂—CN, 4-F H H 7.109 5-F 3-CH(CH₃)CN,4-F H H 7.110 5-F 3-CH₂—CN, 6-F H H 7.111 5-F 3-CH(CH₃)CN, 6-F H H 7.1125-F 3-CH₂—CN, 4-F, 6-F H H 7.113 5-F 3-CH(CH₃)CN, 4-F, H H 6-F 7.114 5-F3-CH₂—CN, 4-Cl, 6-F H H 7.115 5-F 3-CH(CH₃)CN, 4-Cl, H H 6-F 7.116 5-F3-Cl, 6-F H H 7.117 5-F 3-CH₂—CN, 4-CN H H 7.118 5-F 3-CH₂—CN, 4-CH₃ H H7.119 5-F 3-CH(CH₃)CN, H H 4-CH₃ 7.120 5-F 3-Br H H 7.121 5-F 3-I H H7.122 5-F 3-I, 6-F H H 7.123 5-F 3-CH₂—CN, 4-NO₂ H H 7.124 5-F 3-CH₂—CN,4-NH₂ H H 7.125 5-F 3-CHF₂ H H 7.126 5-F 3-CHF₂, 4-F H H 7.127 5-F3-CHF₂, 6-F H H 7.128 5-F 3-CHF₂, 4-F, 6-F H H 7.129 5-CN 3-CH₂CN H H7.130 5-CN 3-CH(CH₃)CN H H 7.131 5-CN 3-Cl H H 7.132 5-CN 3-CH₂—CN, 4-FH H 7.133 5-CN 3-CH(CH₃)CN, 4-F H H 7.134 5-CN 3-CH₂—CN, 6-F H H 7.1355-CN 3-CH(CH₃)CN, 6-F H H 7.136 5-CN 3-CH₂—CN, 4-F, 6-F H H 7.137 5-CN3-CH(CH₃)CN, 4-F, H H 6-F 7.138 5-CN 3-CH₂—CN, 4-Cl, 6-F H H 7.139 5-CN3-CH(CH₃)CN, 4-Cl, H H 6-F 7.140 5-CN 3-Cl, 6-F H H 7.141 5-CN 3-CH₂—CN,4-CN H H 7.142 5-CN 3-CH₂—CN, 4-CH₃ H H 7.143 5-CN 3-CH(CH₃)CN, H H4-CH₃ 7.144 5-CN 3-Br H H 7.145 5-CN 3-I H H 7.146 5-CN 3-I, 6-F H H7.147 5-CN 3-CH₂—CN, 4-NO₂ H H 7.148 5-CN 3-CH₂-CN, 4-NH₂ H H 7.149 5-CN3-CHF₂ H H 7.150 5-CN 3-CHF₂, 4-F H H 7.151 5-CN 3-CHF₂, 6-F H H 7.1525-CN 3-CHF₂, 4-F, 6-F H H 7.153 5-CH₃ 3-CH₂CN H H 7.154 5-CH₃3-CH(CH₃)CN H H 7.155 5-CH₃ 3-Cl H H 7.156 5-CH₃ 3-CH₂—CN, 4-F H H 7.1575-CH₃ 3-CH(CH₃)CN, 4-F H H 7.158 5-CH₃ 3-CH₂—CN, 6-F H H 7.159 5-CH₃3-CH(CH₃)CN, 6-F H H 7.160 5-CH₃ 3-CH₂—CN, 4-F, 6-F H H 7.161 5-CH₃3-CH(CH₃)CN, 4-F, H H 6-F 7.162 5-CH₃ 3-CH₂-CN, 4-Cl, 5-F H H 7.1635-CH₃ 3-CH(CH₃)CN, 4-Cl, H H 5-F 7.164 5-CH₃ 3-Cl, 6-F H H 7.165 5-CH₃3-CH₂—CN, 4-CN H H 7.166 5-CH₃ 3-CH₂—CN, 4-CH₃ H H 7.167 5-CH₃3-CH(CH₃)CN, H H 4-CH₃ 7.168 5-CH₃ 3-Br H H 7.169 5-CH₃ 3-I H H 7.1705-CH₃ 3-I, 6-F H H 7.171 5-CH₃ 3-CH₂—CN, 4-NO₂ H H 7.172 5-CH₃ 3-CH₂—CN,4-NH₂ H H 7.173 5-CH₃ 3-CHF₂ H H 7.174 5-CH₃ 3-CHF₂, 4-F H H 7.175 5-CH₃3-CHF₂, 6-F H H 7.176 5-CH₃ 3-CHF₂, 4-F, 6-F H H 7.177 5-CH₂CH₃ 3-CH₂CNH H 7.178 5-CH₂CH₃ 3-CH(CH₃)CN H H 7.179 5-CH₂CH₃ 3-Cl H H 7.1805-CH₂CH₃ 3-CH₂—CN, 4-F H H 7.181 5-CH₂CH₃ 3-CH(CH₃)CN, 4-F H H 7.1825-CH₂CH₃ 3-CH₂—CN, 6-F H H 7.183 5-CH₂CH₃ 3-CH(CH₃)CN, 6-F H H 7.1845-CH₂CH₃ 3-CH₂—CN, 4-F, 6-F H H 7.185 5-CH₂CH₃ 3-CH(CH₃)CN, 4-F, H H 6-F7.186 5-CH₂CH₃ 3-CH₂—CN, 4-Cl, 6-F H H 7.187 5-CH₂CH₃ 3-CH(CH₃)CN, 4-Cl,H H 6-F 7.188 5-CH₂CH₃ 3-Cl, 6-F H H 7.189 5-CH₂CH₃ 3-CH₂—CN, 4-CN H H7.190 5-CH₂CH₃ 3-CH₂—CN, 4-CH₃ H H 7.191 5-CH₂CH₃ 3-CH(CH₃)CN, H H 4-CH₃7.192 5-CH₂CH₃ 3-Br H H 7.193 5-CH₂CH₃ 3-I H H 7.194 5-CH₂CH₃ 3-I, 6-F HH 7.195 5-CH₂CH₃ 3-CH₂—CN, 4-NO₂ H H 7.196 5-CH₂CH₃ 3-CH₂—CN, 4-NH₂ H H7.197 5-CH₂CH₃ 3-CHF₂ H H 7.198 5-CH₂CH₃ 3-CHF₂, 4-F H H 7.199 5-CH₂CH₃3-CHF₂, 6-F H H 7.200 5-CH₂CH₃ 3-CHF₂, 4-F, 6-F H H 7.201 5-CH(CH₃)₂3-CH₂CN H H 7.202 5-CH(CH₃)₂ 3-CH(CH₃)CN H H 7.203 5-CH(CH₃)₂ 3-Cl H H7.204 5-CH(CH₃)₂ 3-CH₂—CN, 4-F H H 7.205 5-CH(CH₃)₂ 3-CH(CH₃)CN, 4-F H H7.206 5-CH(CH₃)₂ 3-CH₂—CN, 6-F H H 7.207 5-CH(CH₃)₂ 3-CH(CH₃)CN, 6-F H H7.208 5-CH(CH₃)₂ 3-CH₂—CN, 4-F, 6-F H H 7.209 5-CH(CH₃)₂ 3-CH(CH₃)CN,4-F, H H 6-F 7.210 5-CH(CH₃)₂ 3-CH₂—CN, 4-Cl, 5-F H H 7.211 5-CH(CH₃)₂3-CH(CH₃)CN, 4-Cl, H H 5-F 7.212 5-CH(CH₃)₂ 3-Cl, 6-F H H 7.2135-CH(CH₃)₂ 3-CH₂—CN, 4-CN H H 7.214 5-CH(CH₃)₂ 3-CH₂-CN, 4-CH₃ H H 7.2155-CH(CH₃)₂ 3-CH(CH₃)CN, H H 4-CH₃ 7.216 5-CH(CH₃)₂ 3-Br H H 7.2175-CH(CH₃)₂ 3-I H H 7.218 5-CH(CH₃)₂ 3-I, 6-F H H 7.219 5-CH(CH₃)₂3-CH₂—CN, 4-NO₂ H H 7.220 5-CH(CH₃)₂ 3-CH₂—CN, 4-NH₂ H H 7.2215-CH(CH₃)₂ 3-CHF₂ H H 7.222 5-CH(CH₃)₂ 3-CHF₂, 4-F H H 7.223 5-CH(CH₃)₂3-CHF₂, 6-F H H 7.224 5-CH(CH₃)₂ 3-CHF₂, 4-F, 6-F H H 7.225 5-CH₂CH₂CH₃3-CH₂CN H H 7.226 5-CH₂CH₂CH₃ 3-CH(CH₃)CN H H 7.227 5-CH₂CH₂CH₃ 3-Cl H H7.228 5-CH₂CH₂CH₃ 3-CH₂—CN, 4-F H H 7.229 5-CH₂CH₂CH₃ 3-CH(CH₃)CN, 4-F HH 7.230 5-CH₂CH₂CH₃ 3-CH₂—CN, 6-F H H 7.231 5-CH₂CH₂CH₃ 3-CH(CH₃)CN, 6-FH H 7.232 5-CH₂CH₂CH₃ 3-CH₂—CN, 4-F, 6-F H H 7.233 5-CH₂CH₂CH₃3-CH(CH₃)CN, 4-F, H H 6-F 7.234 5-CH₂CH₂CH₃ 3-CH₂—CN, 4-Cl, 6-F H H7.235 5-CH₂CH₂CH₃ 3-CH(CH₃)CN, 4-Cl, H H 6-F 7.236 5-CH₂CH₂CH₃ 3-Cl, 6-FH H 7.237 5-CH₂CH₂CH₃ 3-CH₂—CN, 4-CN H H 7.238 5-CH₂CH₂CH₃ 3-CH₂-CN,4-CH₃ H H 7.239 5-CH₂CH₂CH₃ 3-CH(CH₃)CN, H H 4-CH₃ 7.240 5-CH₂CH₂CH₃3-Br H H 7.241 5-CH₂CH₂CH₃ 3-I H H 7.242 5-CH₂CH₂CH₃ 3-I, 6-F H H 7.2435-CH₂CH₂CH₃ 3-CH₂-CN, 4-NO₂ H H 7.244 5-CH₂CH₂CH₃ 3-CH₂-CN, 4-NH₂ H H7.245 5-CH₂CH₂CH₃ 3-CHF₂ H H 7.246 5-CH₂CH₂CH₃ 3-CHF₂, 4-F H H 7.2475-CH₂CH₂CH₃ 3-CHF₂, 6-F H H 7.248 5-CH₂CH₂CH₃ 3-CHF₂, 4-F, 6-F H H 7.2495-CH═NOCH₃ 3-CH₂CN H H 7.250 5-CH═NOCH₃ 3-CH(CH₃)CN H H 7.251 5-CH═NOCH₃3-Cl H H 7.252 5-CH═NOCH₃ 3-CH₂—CN, 4-F H H 7.253 5-CH═NOCH₃3-CH(CH₃)CN, 4-F H H 7.254 5-CH═NOCH₃ 3-CH₂—CN, 6-F H H 7.255 5-CH═NOCH₃3-CH(CH₃)CN, 6-F H H 7.256 5-CH═NOCH₃ 3-CH₂—CN, 4-F) 6-F H H 7.2575-CH═NOCH₃ 3-CH(CH₃)CN, 4-F) H H 6-F 7.258 5-CH═NOCH₃ 3-CH₂—CN, 4-Cl,6-F H H 7.259 5-CH═NOCH₃ 3-CH(CH₃)CN, 4-Cl, H H 6-F 7.260 5-CH═NOCH₃3-Cl, 6-F H H 7.261 5-CH═NOCH₃ 3-CH₂—CN, 4-CN H H 7.262 5-CH═NOCH₃3-CH₂—CN, 4-CH₃ H H 7.263 5-CH═NOCH₃ 3-CH(CH₃)CN, H H 4-CH₃ 7.2645-CH═NOCH₃ 3-Br H H 7.265 5-CH═NOCH₃ 3-I H H 7.266 5-CH═NOCH₃ 3-I, 6-F HH 7.267 5-CH═NOCH₃ 3-CH₂—CN, 4-NO₂ H H 7.268 5-CH═NOCH₃ 3-CH₂-CN, 4-NH₂H H 7.269 5-CH═NOCH₃ 3-CHF₂ H H 7.270 5-CH═NOCH₃ 3-CHF₂, 4-F H H 7.2715-CH═NOCH₃ 3-CHF₂, 6-F H H 7.272 5-CH═NOCH₃ 3-CHF₂, 4-F, 6-F H H 7.273 H(n = 0) 3-CHF₂, 4-F, 6-F H H 7.274 H (n = 0) 3-CHF₂, 4-Cl, 6-F H H 7.275H (n = 0) 3-CHF₂, 4-F H H 7.276 H (n = 0) 3-CHF₂, 6-F H H 7.277 H (n =0) 3-CHF₂ H H 7.278 H (n = 0) 3-CH₂—CN, 4-F, 6-F H H 7.279 H (n = 0)3-CH₂—CN, 4-Cl, 6-F H H 7.280 H (n = 0) 3-CH₂—CN, 4-F H H 7.281 H (n =0) 3-CH₂—CN, 6-F H H 7.282 H (n = 0) 3-CH₂—CN H H 7.283 H (n = 0)3-CH(CH₃)CN, H H 4-F, 6-F 7.284 H (n = 0) 3-CH(CH₃)CN, H H 4-F 7.285 H(n = 0) 3-CH(CH₃)CN, H H 6-F 7.286 H (n = 0) 3-CH(CH₃)CN H H 7.287 H (n= 0) 3-Cl H H 7.288 H (n = 0) 3-Br H H 7.289 H (n = 0) 3-F H H 7.290 H(n = 0) 3-CH₃ H H 7.291 H (n = 0) 3-I H H

TABLE 8 Compounds of formula Ie₆1: (Ie₆1)

Phys. data Comp. m.p. no. R₁ R₂ R₃ R₄ (° C.) 8.001 3-CN, 5-OCH₃ 3-CH₂—CNH H 8.002 3-Cl, 5-F 3-CH₂—CN H H 8.003 3-Cl, 5-Cl 3-CH₂—CN H H 8.0043-F, 5-OCH₃ 3-CH₂—CN H H 8.005 3-Cl, 5-OCH₃ 3-CH₂—CN H H 8.006 3-Br,5-OCH₃ 3-CH₂—CN H H 8.007 3-CF₃, 5-Cl 3-CH₂—CN H H 8.008 3-CF₃, 5-OCH₃3-CH₂—CN H H 8.009 3-CH₃, 5-OCH₃ 3-CH₂—CN H H 8.010 3-CH═NOCH₃, 5-OCH₃3-CH₂—CN H H 8.011 3-CF₃, 5-F 3-CH₂—CN H H 8.012 5-OCH₃ 3-CH₂—CN H H8.013 5-OCH₃ 3-CH₂—CN F F 8.014 5-OCH₃ 3-CHF₂ H H 8.015 5-OCH₃ 3-CHF₂,4-F H H 8.016 H (n = 0) 3-CH₂—CN H H 8.017 H (n = 0) 3-CHF₂ H H 8.018 H(n = 0) 3-CHF₂, 4-F H H 8.019 H (n = 0) 3-CH₂—CN, 4-F H H

TABLE 9 Compounds of formula Ic₃1: (Ic₃1)

Comp. Phys. data no. R₁ R₂ R₃ R₄ m.p. (° C.) 9.001 6-Cl 3-Cl H H 83-849.002 6-Cl 4-Cl H H solid 9.003 6-Cl 3-CH₂—CN H H 97-98 9.004 4-OCH₃3-CH₂—CN H H 9.005 4-OCH₃ 4-Cl H H 9.006 4-OCH₃ 3-Cl H H 9.007 4-OCH₃3-CH₂—CN, 4-F H H 9.008 4-OCH₃ 3-CH₂—CN, 4-Cl H H 9.009 4-OCH₃ 3-CH₂—CN,4-CH₃ H H 9.010 4-OCH₃ 3-CH₂—CN, 4-Cl, 6-F H H 9.011 4-OCH₃, 6-Cl3-CH₂—CN H H 9.012 4-OCH₃, 6-Cl 4-Cl H H 9.013 4-OCH₃, 6-Cl 3-Cl H H9.014 4-OCH₃, 6-Cl 3-CH₂—CN, 4-F H H 9.015 4-OCH₃, 6-Cl 3-CH₂—CN, 4-Cl HH 9.016 4-OCH₃, 6-Cl 3-CH₂—CN, 4-CH₃ H H 9.017 4-OCH₃, 6-Cl 3-CH₂—CN,4-Cl, 6-F H H 9.018 4-F 3-CH₂—CN H H 9.019 4-F, 6-Cl 3-CH₂—CN H H 9.0204-F, 6-CF₃ 3-CH₂—CN H H 9.021 4-F, 6-Br 3-CH₂—CN H H 9.022 4-Cl, 6-Cl3-CH₂—CN H H 9.023 4-Cl 3-CH₂—CN H H 9.024 6-F 3-CH₂—CN H H 9.0254-OCH₃, 6-CF₃ 3-CH₂—CN, 4-F H H 9.026 4-OCH₃, 6-CF₃ 3-CH₂—CN H H 9.0274-OCH₃, 6-Cl 3-CH₂—CN, 6-F H H 9.028 4-F, 6-Cl 3-CH₂—CN, 6-F H H 9.0294-F, 6-Cl 3-CH₂—CN, 4-F H H 9.030 4-F, 6-Cl 3-CHF₂, 6-F H H 9.0314-OCH₃, 6-Cl 3-CHF₂, 4-F H H 9.032 4-F, 6-Cl 3-CHF₂ H H 9.033 4-OCH₃,6-Cl 3-CHF₂ H H 9.034 4-OCH₃ 3-CHF₂ H H 9.035 4-OCH₃ 3-CHF₂, 6-F H H9.036 4-OCH₃ 3-CHF₂, 4-F H H 9.037 4-OCH₃ 3-CHF₂, 4-F, 6-F H H 9.0384-OCH₃ 3-CHF₂, 4-Cl, 6-F H H 9.039 4-OCH₃, 6-Cl 3-CHF₂, 6-F H H 9.0404-OCH₃, 6-Cl 3-CHF₂, 4-F, 6-F H H 9.041 4-OCH₃, 6-Cl 3-CHF₂, 4-Cl, 6-F HH

BIOLOGICAL EXAMPLES Example B1 Herbicidal Action Prior to Emergence ofthe Plants (Pre-Emergence Action)

Monocotyledonous and dicotyledonous test plants are sown in standardsoil in pots. Immediately after sowing, the test compounds, in the formof an aqueous suspension (prepared from a wettable powder (Example F3,b) according to WO 97/34485) or in the form of an emulsion (preparedfrom an emulsifiable concentrate (Example F1, c) according to WO97/34485), are applied by spraying, in an optimum concentration (500litres of water per ha). The test plants are then grown in a greenhouseunder optimum conditions.

After a test duration of 4 weeks, the test is evaluated in accordancewith a scale of nine ratings (1=total damage, 9=no action). Ratings offrom 1 to 4 (especially from 1 to 3) indicate good to very goodherbicidal action.

Test plants: Panicum (Pani), Digitaria (Digit), Euphorbia (Euph), Sida,Abutilon (Abut), Amaranthus (Amar), Chenopodium (Cheno), Stellaria(Stell). TABLE B1 Concentration: 1000 g of active compound per ha Testplant: Comp. no. Pani Digit Euph Sida Abut Amar Cheno Stell 1.041 1 1 11 1 1 1 1 1.048 4 2 1 1 1 1 1 1 7.006 2 — 1 — 2 — 1 1 7.022 1 1 3 1 1 13 1

The same results are obtained when the compounds of formula I areformulated analogously to the other Examples of WO 97/34485.

Example B2 Post-Emergence Herbicidal Action

Monocotyledonous and dicotyledonous test plants are sown in standardsoil in pots. When the test plants are at the 2- to 3-leaf stage, thetest compounds, in the form of an aqueous suspension (prepared from awettable powder (Example F3, b) according to WO 97/34485) or in the formof an emulsion (prepared from an emulsifiable concentrate (Example F1,c) according to WO 97/34485), are applied by spraying, in an optimumconcentration (500 litres of water per ha). The test plants are thengrown on in a greenhouse under optimum conditions.

After a test duration of 2 to 3 weeks, the test is evaluated inaccordance with a scale of nine ratings (1=total damage, 9=no action).Ratings of from 1 to 4 (especially from 1 to 3) indicate good to verygood herbicidal action.

Test plants. Panicum (Pani), Euphorbia (Euph), Abutilon (Abut),Amaranthus (Amara), Stellaria (Stell), Veronica (Vero). TABLE B2Concentration: 1000 g of active compound per ha Test plant: Comp. no.Pani Euph Abut Amar Stell Vero 1.041 2 1 2 2 2 2 1.048 4 1 3 1 2 2 4.0332 2 3 3 2 4 5.025 2 1 1 4 1 4 7.006 5 1 3 2 4 5 7.008 2 2 2 2 2 2 7.0212 1 2 1 3 3 7.022 2 1 — 1 3 2 7.027 1 2 4 2 3 4 7.028 — 1 — 1 1 2 7.0312 3 3 2 3 2

In the two Tables above, “-” means that there are no data available forthe compounds and weeds in question.

The same results are obtained when the compounds of formula I areformulated analogously to the other Examples of WO 97/34485.

1. A compound of formula I

wherein Q is a group

Z is ═N—,

 or ═C(R₂)—; n is 0, 1, 2 or 3; each R₁ independently is halogen, —CN,—SCN, —SF₅, —NO₂, —NR₅R₆, —CO₂R₇, —CONR₈R₉, —C(R₁₀)═NOR₁₁, —COR₁₂,—OR₁₃, —SR₁₄, —SOR₁₅, —SO₂R₁₆, —OSO₂R₁₇, C₁-C₈alkyl, C₂-C₈alkenyl,C₂-C₈alkynyl or C₃-C₆cycloalkyl; or is C₁-C₈alkyl, C₂-C₈alkenyl orC₂-C₈alkynyl mono- to penta-substituted by halogen or mono-, di- ortri-substituted by —CN, —NO₂, —NR₁₈R₁₉, —CO₂R₂₀, —CONR₂₁R₂₂, —COR₂₃,—C(R₂₄)═NOR₂₅, —C(S)NR₂₆R₂₇, —C(C₁-C₄alkylthio)═NR₂₈, —OR₂₉, —SR₃₀,—SOR₃₁, —SO₂R₃₂ or by C₃-C₆cycloalkyl; or each R₁ independently isC₃-C₆cycloalkyl mono- to penta-substituted by halogen or mono-, di- ortri-substituted by —CN, —NO₂, —NR₁₈R₁₉, —CO₂R₂₀, —CONR₂₁R₂₂, —COR₂₃,—C(R₂₄)═NOR₂₅, —C(S)NR₂₆R₂₇, —C(C₁-C₄alkylthio)═NR₂₈, —SR₃₀, —SOR₃₁,—SO₂R₃₂ or by C₃-C₆cycloalkyl; or each R₁ independently is phenyl whichmay in turn be mono- to penta-substituted by halogen or by C₁-C₄alkyl ormono-, di- or tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or, when Qis a group Q₁, Q₂, Q₃ or Q₅ to adjacent R₁ substituents may togetherform a C₁-C₇alkylene bridge which may be interrupted by from 1 to 3hetero atoms selected from oxygen, nitrogen and sulfur and which may bemono- to penta-substituted by halogen or by C₁-C₆alkyl or mono-, di- ortri-substituted by C₁-C₆alkoxy, the total number of ring atoms being atleast 5 and at most 9; or, when Q is a group Q₁, Q₂, Q₃ or Q₅, twoadjacent R₁ substituents may together form a C₂-C₇alkenylene bridgewhich may be interrupted by from 1 to 3 hetero atoms selected fromoxygen, nitrogen and sulfur and which may be mono- to penta-substitutedby halogen or by C₁-C₆alkyl or mono-, di- or tri-substituted byC₁-C₆alkoxy, the total number of ring atoms being at least 5 and at most9; R₃ or R₄ are each independently of the other hydrogen, halogen, —CN,C₁-C₄alkyl or C₁-C₄alkoxy; or R₅ is hydrogen or C₁-C₈alkyl; R₆ ishydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, itbeing possible for phenyl and benzyl in turn to be mono- topenta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₅ andR₆ together are a C₂-C₅alkylene chain which may be interrupted by anoxygen or sulfur atom; R₇ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl orC₃-C₈alkynyl, or is C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl mono- topenta-substituted by halogen or mono-, di- or tri-substituted byC₁-C₄alkoxy or by phenyl, it being possible for phenyl in turn to bemono- to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₈ ishydrogen or C₁-C₈alkyl; R₉ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkylmono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN,or R₉ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being possiblefor phenyl and benzyl in turn to be mono- to penta-substituted byhalogen or by C₁-C₄alkyl or mono-, di- or tri-substituted byC₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₈ and R₉ together areC₂-C₅alkylene; R₁₀ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl orC₃-C₆cycloalkyl; R₁₁ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl, C₁-C₄haloalkyl or C₃-C₆haloalkenyl; R₁₂ is hydrogen,C₁-C₄alkyl, C₁-Q₄haloalkyl or C₃-C₆cycloalkyl; R₁₃ is hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl; or R₁₃ is phenyl orphenyl-C₁-C₆alkyl, it being possible for the phenyl ring in turn to bemono- to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by C₁-C₈alkylsulfonyl, or R₁₃ isC₁-C₈alkyl mono- to penta-substituted by halogen or mono-, di- ortri-substituted by CN, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino or byC₁-C₄alkoxy; R₁₄ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl,or is C₁-C₈alkyl mono- to penta-substituted by halogen or mono-, di- ortri-substituted by —CN or by C₁-C₄alkoxy; R₁₅, R₁₈ and R₁₇ are eachindependently of the others C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, orC₁-C₈alkyl mono- to penta-substituted by halogen or mono-, di- ortri-substituted by —CN or by C₁-C₄alkoxy; R₁₈ is hydrogen or C₁-C₈alkyl;R₁₉ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl orbenzyl, it being possible for phenyl and benzyl in turn to be mono- topenta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₁₈ andR₁₉ together are a C₂-C₅alkylene chain which may be interrupted by anoxygen or sulfur atom; R₂₀ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl, phenyl or benzyl, it being possible for phenyl and benzylin turn to be mono- to penta-substituted by halogen or by C₁-C₄alkyl ormono-, di- or tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₂₁ ishydrogen or C₁-C₈alkyl; R₂₂ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkylmono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN,or R₂₂ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it beingpossible for phenyl and benzyl in turn to be mono- to penta-substitutedby halogen or by C₁-C₄alkyl or mono-, di- or tri-substituted byC₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₂₁ and R₂₂ together areC₂-C₅alkylene; R₂₃ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl orC₃-C₆cycloalkyl; R₂₄ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl orC₃-C₆cycloalkyl; R₂₅ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl, C₁-C₄haloalkyl or C₃-C₆haloalkenyl; R₂₆ is hydrogen orC₁-C₈alkyl; R₂₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di-or tri-substituted by —COOH, C₁-C₈-alkoxycarbonyl or by —CN, or R₂₇ isC₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being possible forphenyl and benzyl in turn to be mono- to penta-substituted by halogen orby C₁-C₄alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; or R₂₆ and R₂₇ together are C₂-C₅alkylene; R₂₈ ishydrogen or C₁-C₈alkyl; R₂₉ and R₃₀ are each independently of the otherhydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono-to penta-substituted by halogen or mono-, di- or tri-substituted by —CNor by C₁-C₄alkoxy; R₃₁ and R₃₂ are each independently of the otherC₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono- topenta-substituted by halogen or mono-, di- or tri-substituted by —CN or,by C₁-C₄alkoxy; m is 0, 1, 2, 3 or 4; each R₂ independently is halogen,—CN, —SCN, —OCN, —N₃, —SF₅, —NO₂, —NR₃₃R₃₄, —CO₂R₃₅, —CONR₃₆R₃₇,—C(R₃₈)═NOR₃₉, —COR₄₀, —OR₄₁, —SR₄₂, —SOR₄₃, —SO₂R₄₄, —OSO₂R₄₅,—N([CO]_(p)R₄₆)COR₄₇, —N(OR₅₄)COR₅₅, —N(R₅₆)SO₂R₅₇, —N(SO₂R₅₈)SO₂R₅₉,—N═C(OR₆₀)R₆₁, —CR₆₂(OR₆₃)OR₆₄, —OC(O)NR₆₅R₆₆, —SC(O)NR₆₇R₆₈,—OC(S)NR₆₉R₇₀ or —N-phthalimide; or R₂ is a 5- to 7-memberedheterocyclic ring system which may be aromatic or partially or fullysaturated and may contain from 1 to 4 hetero atoms selected fromnitrogen, oxygen and sulfur, it being possible for that heterocyclicring system in turn to be mono- to penta-substituted by halogen or byC₁-C₄alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy, C₁-C₄alkoxy-C₁-C₄alkyl, —CN, —NO₂,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl or by C₁-C₆alkylsulfonyl; R₃₃ ishydrogen or C₁-C₈alkyl; and R₃₄ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl, phenyl or benzyl, it being possible for phenyl and benzylin turn to be mono- to penta-substituted by halogen or by C₁-C₄alkyl ormono-, di- or tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₃₃ andR₃₄ together are a C₂-C₅alkylene chain which may be interrupted by anoxygen or sulfur atom; R₃₅ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl orC₃-C₈alkynyl, or is C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl mono- topenta-substituted by halogen or mono-, di- or tri-substituted byC₁-C₄alkoxy or by phenyl, it being possible for phenyl in turn to bemono- to penta-substituted by halogen or by C₁G₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl; C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₃₆ishydrogen or C₁-C₈alkyl; R₃₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkymono-, di- or tri-substituted by —COOH, C₁-C₈-alkoxycarbonyl or by —CN,or R₃₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it beingpossible for phenyl and benzyl int turn to be mono- to penta-substitutedby halogen or by C₁-C₄alkyl or mono-, dl- or tri-substituted byC₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₃₆ and R₃₇ together areC₃-C₅alkylene; R₃₈ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl orC₃-C₆cycloalkyl; R₃₉ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl, C₁-C₄haloalkyl or C₃-C₆haloalkenyl; R₄₀ is hydrogen,C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₈alkylthio, —C(O)—C(O)OC₁-C₄alkyl orC₃-C₆-cycloalkyl; R₄₁ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl, C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₈alkylcarbonyl,C₁-C₈alkoxycarbonyl, C₃-C₈alkenyloxycarbonyl,C₁-C₆alkoxy-C₁-C₆alkoxycarbonyl, C₁-C₆alkylthio-C₁-C₆alkyl,C₁-C₆alkylsulfinyl-C₁-C₆alkyl or C₁-C₆alkylsulfonyl-C₁-C₆alkyl; or R₄₁is phenyl or phenyl-C₁-C₆alkyl, it being possible for the phenyl ring inturn to be mono- to penta-substituted by halogen or by C₁-C₄alkyl ormono-, di- or tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂or by —S(O)₂C₁-C₈alkyl, or R₄₁ is C₁-C₈alkyl mono- to penta-substitutedby halogen or mono-, di- or tri-substituted by —COOH,C₁-C₈alkoxycarbonyl, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino or by —CN; R₄₂is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkylmono- to penta-substituted by halogen or mono-, di- or tri-substitutedby —CN or by C₁-C₄alkoxy; R₄₃ and R₄₄ are each independently of theother C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₈alkyl mono- topenta-substituted by halogen or mono-, di- or tri-substituted by —CN orby C₁-C₄alkoxy; R₄₅ is C₁-C₈alkyl, C₁-C₈alkyl mono- to penta-substitutedby halogen or mono-, di- or tri-substituted by —CN or by C₁-C₄alkoxy, oris C₃-C₈alkenyl or C₃-C₈alkynyl, or R₄₅ is phenyl, it being possible forthe phenyl ring to be mono- to penta-substituted by halogen or byC₁-C₄alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, NO₂, C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or byC₁-C₈alkylsulfonyl; R₄₆ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl or C₁-C₄haloalkyl; R₄₇ is hydrogen, C₁-C₈alkyl,C₁-C₄alkoxy, C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl mono- topenta-substituted by halogen or mono-, di- or tri-substituted by —CN,C₁-C₄alkoxy, C₁-C₈alkoxycarbonyl, —NH₂, C₁-C₄alkylamino,di(C₁-C₄alkyl)amino, —NR₄₈COR₄₉, —NR₅₀SO₂R₅₁ or by —NR₅₂CO₂R₅₃, or R₄₇is phenyl or benzyl, it being possible for phenyl and benzyl in turn tobe mono- to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di-or tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; p is 0 or1; R₄₈, R₄₉, R₅₀, R₅₁, R₅₂ and R₅₃ are each independently of the othershydrogen, C₁-C₈alkyl, phenyl, benzyl or naphthyl, it being possible forthe three last mentioned aromatic radicals in turn to be mono- topenta-substituted by halogen or by C₁-C₈alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄alkylamino,di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinylor by C₁-C₄alkylsulfonyl; R₅₄ and R₅₅ are each independently of theother hydrogen, C₁-C₈alkyl, or phenyl which may in turn be mono- topenta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by C₁-C₈alkylsulfonyl; R₅₆ ishydrogen, C₁-C₈alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₃-C₈alkenyl,C₃-C₈alkynyl or benzyl, it being possible for benzyl in turn to be mono-to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by C₁-C₈alkylsulfonyl; R₅₇ isC₁-C₈alkyl, C₁-C₄haloalkyl, phenyl, benzyl or naphthyl, it beingpossible for the last three aromatic rings to be mono- topenta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄alkylamino,di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinylor by C₁-C₄alkylsulfonyl; R₅₈ and R₅₉ are each independently of theother C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl, benzyl ornaphthyl, it being possible for the last three aromatic rings to bemono- to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄alkylamino,di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinylor by C₁-C₄alkylsulfonyl; R₆₀ and R₆₁ are each independently of theother hydrogen or C₁-C₆alkyl; R₆₂, R₆₃ and R₆₄ are each independently ofthe others hydrogen or C₁-C₈alkyl, or R₆₃ and R₆₄ together form aC₂-C₅alkylene bridge; R₆₅, R₆₆, R₆₇, R₆₈, R₆₉ and R₇₀ are eachindependently of the others hydrogen or C₁-C₈alkyl, or R₆₅ and R₆₆, orR₆₇ and R₆₈, or R₆₉ and R₇₀ in each case together form a C₂-C₅alkylenebridge; or each R₂ independently is C₁-C₂alkyl, or is C₁-C₈alkyl mono-to penta-substitution by halogen or mono-, di- or tri-substituted by—CN, —N₃, —SCN, —NO₂, —NR₇₁R₇₂, —CO₂R₇₃, —CONR₇₄R₇₅, —COR₇₆,—C(R₇₇)═NOR₇₈, —C(S)NR₇₉R₈₀, —C(C₁-C₄alkylthio)═NR₈₁, —OR₈₂, —SR₈₃,—SOR₈₄, —SO₂R₈₅, —O(SO₂)R₈₆, —N(R₈₇)CO₂R₈₈, —N(R₈₉)COR₉₀, —S⁺(R₉₁)₂,—N⁺(R₉₂)₃, —Si(R₉₃)₃ or by C₃-C₆cycloalkyl; or each R₂ independently isC₁-C₈alkyl substituted by a 5- to 7-membered heterocyclic ring systemwhich may be aromatic or partially or fully saturated and may containfrom 1 to 4 hetero atoms selected from oxygen, nitrogen and sulfur, itbeing possible for that heterocyclic ring system in turn to be mono- topenta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy,C₁-C₄alkoxy-C₁-C₄alkyl, —CN, —NO₂, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl orby C₁-C₆alkylsulfonyl; or each R₂ independently is C₂-C₈alkenyl, or isC₂-C₈alkenyl mono- to penta-substituted by halogen or mono-, di- ortri-substituted by —CN, —NO₂, —CO₂R₉₄, —CONR₉₅R₉₆, —COR₉₇,—C(R₉₈)═NOR₉₉, —C(S)NR₁₀₀R₁₀₁, —C(C₁-C₄alkylthio)═NR₁₀₂, —OR₁₀₃,—Si(R₁₀₄)₃ or by C₃-C₆-cycloalkyl; or each R₂ independently isC₂-C₈alkynyl, or is C₂-C₈alkynyl mono- to penta-substituted by halogenor mono-, di- or tri-substituted by —CN, —CO₂R₁₀₅, —CONR₁₀₆R₁₀₇,—COR₁₀₈, —C(R₁₀₉)═NOR₁₁₀, —C(S)NR₁₁₁R₁₁₂, —C(C₁-C₄alkylthio)═NR₁₁₃,—OR₁₁₄, —Si(R₁₁₅)₃ or by C₃-C₆cycloalkyl; or each R₂ independently isC₃-C₆cycloalkyl, or is C₃-C₆cycloalkyl mono- to penta-substituted byhalogen or mono-, di- or tri-substituted by —CN, —CO₂R₁₁₆, —CONR₁₁₇R₁₁₈,—COR₁₁₉, —C(R₁₂₀)═NOR₁₂₁, —C(S)NR₁₂₂R₁₂₃ or by —C(C₁-C₄alkylthio)═NR₁₂₄;or two adjacent R₂ substituents together form a C₁-C₇alkylene bridgewhich may be interrupted by from 1 to 3 hetero atoms selected fromoxygen, nitrogen and sulfur and may be mono- to penta-substituted byhalogen or by C₁-C₆alkyl or mono-, di- or tri-substituted byC₁-C₆alkoxy, the total number of ring atoms being at least 5 and at most9; or two adjacent R₂ substituents together form a C₂-C₇alkenylenebridge which may be interrupted by from 1 to 3 hetero atoms selectedfrom oxygen, nitrogen and sulfur and may be mono- to penta-substitutedby halogen or by C₁-C₆alkyl or mono-, di- or tri-substituted byC₁-C₆alkoxy, the total number of ring atoms being at least 5 and at most9; R₇₁ is hydrogen or C₁-C₈alkyl; R₇₂ is hydrogen, C₁-C₈alkyl,C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being possible forphenyl and benzyl in turn to be mono- to penta-substituted by halogen orby C₁-C₄alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; or R₇₁ and R₇₂ together are a C₂-C₅alkylene obainwhich may be interrupted by an oxygen or sulfur atom; R₇₃ is hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl, C₃-C₈alkenylor C₃-C₈alkynyl mono- to penta-substituted by halogen or mono-, di- ortri-substituted by C₁-C₄alkoxy or by phenyl, it being possible for henylin turn to be mono- to penta-substituted by halogen or by C₁-C₄alkyl ormono-, di- or tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₇₄ ishydrogen or C₁-C₈alkyl; R₇₅ is hydrogen, C₁-C₈alkyl or C₃-C₈cycloalkyl,or is C₁-C₈alkyl mono-, di- or tri-substituted by —COOH,C₁-C₈alkoxycarbonyl, C₁-C₆alkoxy or by —CN; or R₇₅ is C₃-C₈alkenyl,C₃-C₈alkynyl, phenyl or benzyl, it being possible for phenyl and benzylin turn to be mono- to penta-substituted by halogen or by C₁-C₄alkyl ormono-, di- or tri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio; C₁-C₄alkylsufinyl; or R₇₄ and R₇₅ together are aC₂-C₅alkylene chain which may be interrupted by an oxygen or sulfuratom; R₇₆ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl;R₇₇ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₇₈ ishydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₄haloalkyl orC₃-C₆haloalkenyl; and R₇₉ is hydrogen or C₁-C₈alkyl; R₈₀ is hydrogen orC₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by —COOH,C₁-C₈-alkoxycarbonyl or by —CN; or R₈₀ is C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono- to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₇₉ andR₈₀ together are C₂-C₅alkylene; R₈₁ is hydrogen or C₁-C₈alkyl; R₈₂ is—Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl whichis mono- to penta-substituted by halogen or mono-, di- ortri-substituted by —CN, —NH₂, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino or byC₁-C₄alkoxy; R₈₃ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl,or is C₁-C₈alkyl which is mono- to penta-substituted by halogen ormono-, di- or tri-substituted by —CN, —NH₂, C₁-C₆alkylamino,di(C₁-C₆alkyl)amino or by C₁-C₄alkoxy; R₈₄, R₈₅ and R₈₆ are eachindependently of the others C₁-C₆alkyl, C₃-C₈-alkenyl or C₃-C₈-alkynyl,or C₁-C₈alkyl which is mono- to penta-substituted by halogen or mono-,di- or tri-substituted by —CN or by C₁-C₄alkoxy; R₈₇ and R₈₉ are eachindependently of the other hydrogen; C₁-C₈alkyl or C₁-C₈alkoxy; R₈₈ isC₁-C₈alkyl; R₉₀ is hydrogen or C₁-C₈alkyl; R₉₁ is C₁-C₄alkyl; R₉₂ andR₉₃ are each independently of the other C₁-C₆alkyl; R₉₄ is hydrogen oris C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, each of which may be mono-to penta-substituted by halogen or mono-, di- or tri-substituted byC₁-C₄alkoxy or by phenyl, it being possible for phenyl in turn to bemono- to penta-substituted by halogen or by C₁-C₄-alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₉₅ ishydrogen or C₁-C₈alkyl; R₉₆ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkylmono-, di- or tri-substituted by —COOH, C₁-C₃alkoxycarbonyl or by —CN;or R₉₆ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it beingpossible for phenyl and benzyl in turn to be mono- to penta-substitutedby halogen or by C₁-C₄alkyl or mono-, di- or tri-substituted byC₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₉₅ and R₉₆ together areC₂-C₅alkylene; R₉₇ and R₉₈ are each independently of the other hydrogen,C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₉₉ is hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₄haloalkyl orC₃-C₈haloalkenyl; R₁₀₀ is hydrogen or C₁-C₈alkyl; R₁₀₁ is hydrogen orC₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by —COOH,C₁-C₈-alkoxycarbonyl or by —CN; or R₁₀₁ is C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono- to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₁₀₀ andR₁₀₁ together are C₂-C₅alkylene; R₁₀₂ is hydrogen or C₁-C₈alkyl; R₁₀₃ ishydrogen, C₁-C₈alkyl, —Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or C₃-C₈alkynyl;R₁₀₄ is C₁-C₆alkyl; R₁₀₅ is hydrogen or is C₃-C₈alkyl, C₃-C₈alkenyl orC₃-C₈alkynyl, each of which may be mono- to penta-substituted by halogenor mono-, di- or tri-substituted by C₁-C₄alkoxy or by phenyl it beingpossible for phenyl in turn to be mono- to penta-substituted by halogenor by C₁-C₄-alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; R₁₀₆ is hydrogen or C₁-C₈alkyl; R₁₀₇ is hydrogen orC₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by —COOH,C₁-C₈alkoxycarbonyl or by —CN, or R₁₀₇ is C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono- to penta-substituted by halogen or by C₁-C₄alkyl or mono; di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₁₀₆ andR₁₀₇ together are C₂-C₅alkylene; R₁₀₈ is hydrogen, C₁-C₄alkyl,C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₁₀₉ is hydrogen, C₁-C₄alkyl,C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₁₁₀ is hydrogen, C₁-C₈alkyl,C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₄haloalkyl or C₃-C₆haloalkenyl; R₁₁₁ ishydrogen or C₁-C₈alkyl; R₁₁₂ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkylmono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN;or R₁₁₂ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it beingpossible for phenyl and benzyl in turn to be mono- to penta-substitutedby halogen or by C₁-C₄alkyl or mono-, di- or tri-substituted byC₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₁₁₁ and R₁₁₂ togetherare C₂-C₅alkylene; R₁₁₃ is hydrogen or C₁-C₈alkyl; R₁₁₄ is hydrogen,C₁-C₈alkyl, —Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or C₃-C₈alkynyl; R₁₁₅ isC₁-C₆alkyl; R₁₁₆ is hydrogen or is C₁-C₈alkyl, C₃-C₈alkenyl orC₃-C₈alkynyl, each of which may be mono- to penta-substituted by halogenor mono-, di- or tri-substituted by C₁-C₄alkoxy or by phenyl, it beingpossible for phenyl in turn to be mono- to penta-substituted by halogenor by C₁-C₄-alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; R₁₁₇ is hydrogen or C₁-C₈alkyl; R₁₁₈ is hydrogen orC₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by —COOH,C₁-C₈alkoxycarbonyl or by —CN; or R₁₁₈ is C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono- to penta-substituted by halogen or by C₁-C₄alkyl or mono-, di- ortri-substituted by C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₁₁₇ and R₁₁₈ togetherare C₂-C₅alkylene; R₁₁₉ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl orC₃-C₆cycloakyl; R₁₂₀ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl orC₃-C₆cycloalkyl; R₁₂₁ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl, C₁-C₄haloalkyl or C₃-C₆haloalkenyl; R₁₂₂ is hydrogen orC₁-C₈alkyl; R₁₂₃ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di-or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or R₁₂₃ isC₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being possible forphenyl and benzyl in turn to be mono- to penta-substituted by halogen orby C₁-C₄alkyl or mono-, di- or tri-substituted by C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; or R₁₂₂ and R₁₂₃ together are C₂-C₅alkylene; andR₁₂₄ is hydrogen or C₁-C₈alkyl, or an agrochemically acceptable salt orany stereoisomer or tautomer of a compound of formula I.
 2. A compoundof formula I wherein each R₁ independently is halogen, —CN, —SCN, —SF₅,—NO₂, —NR₅R₆, —CO₂R₇, —CONR₈R₉, —C(R₁₀)═NOR₁₁, —COR₁₂, —OR₁₃, —SR₁₄,—SOR₁₅, —SO₂R₁₆, —OSO₂R₁₇, C₁-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl orC₃-C₆cycloalkyl; or is C₁-C₈alkyl, C₂-C₈alkenyl or C₂-C₈alkynyl mono-,di- or tri-substituted by halogen, —CN, —NO₂, —NR₁₈R₁₉, —CO₂R₂₀,—CONR₂₁R₂₂, —COR₂₃, —C(R₂₄)═NOR₂₅, —C(S)NR₂₆R₂₇,—C(C₁-C₄alkylthio)═NR₂₈, —OR₂₉, —SR₃₀, —SOR₃₁, —SO₂R₃₂ or byC₃-C₆cycloalkyl; or each R₁ independently is C₃-C₆cycloalkyl mono-, di-or tri-substituted by halogen, —CN, —NO₂, —NR₁₈R₁₉, —CO₂R₂₀, —CONR₂₁R₂₂,—COR₂₃, —C(R₂₄)═NOR₂₅, —C(S)NR₂₆R₂₇, —C(C₁-C₄alkylthio)═NR₂₈, —SR₃₀,—SOR₃₁, —SO₂R₃₂ or by C₃-C₆cycloalkyl; or each R₁ independently isphenyl which may in turn be mono-, di- or tri-substituted by halogen,C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or, when Q is a group Q₁,Q₂, Q₃ or Q₅, two adjacent R₁ substituents together may form aC₁-C₇alkylene bridge which may be interrupted by from 1 to 3 heteroatoms selected from oxygen, nitrogen, and sulfur and may be mono-, di-or tri-substituted by halogen, C₁-C₆alkyl or by C₁-C₆alkoxy, the totalnumber of ring atoms being at least 5 and at most 9; or, when Q is agroup Q₁, Q₂, Q₃ or Q₅, two adjacent R₁ substitutents together may forma C₂-C₇alkenylene bridge which may be interrupted by from 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur and may be mono-, di- ortri-substituted by halogen, C₁-C₆alkyl or by C₁-C₆alkoxy, the totalnumber of ring atoms being at least 5 and at most 9; R₃ or R₄ are eachindependently of the other hydrogen, halogen, —CN, C₁-C₄alkyl orC₁-C₄alkoxy; or R₃ and R₄ together are C₂-C₅alkylene; R₅ is hydrogen orC₁-C₈alkyl; R₆ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono-, di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; or R₅ and R₆ together are a C₂-C₅alkylene chainwhich, may be interrupted by an oxygen or sulfur atom; R₇ is hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl, C₃-C₈alkenylor C₃-C₈alkynyl mono-, di- or tri-substituted by halogen, C₁-C₄alkoxy orby phenyl, it being possible for phenyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄-haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;R₈ is hydrogen or C₁-C₈alkyl; R₉ is hydrogen or C₁-C₈alkyl, or isC₁-C₈alkyl mono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonylor by —CN, or R₉ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, itbeing possible for phenyl and benzyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;or R₈ and R₉ together are C₂-C₅alkylene; R₁₀ is hydrogen, C₁-C₄alkyl,C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₁₁ is hydrogen, C₁-C₈alkyl,C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₄haloalkyl or C₃-C₆haloalkenyl; R₁₂ ishydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₁₃ ishydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl; or R₁₃ is phenyl orphenyl-C₁-C₆alkyl, it being possible for the phenyl ring in turn to bemono-, di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₈-alkylthio, C₁-C₈alkylsulfinyl or byC₁-C₈alkylsulfonyl; or R₁₃ is C₁-C₈alkyl mono-, di- or tri-substitutedby halogen, —CN, C₁-C₆alkylamino, di(C₁-C₆-alkyl)amino or byC₁-C₄alkoxy; R₁₄ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl,or is C₁-C₈alkyl mono-, di- or tri-substituted by halogen, —CN or byC₁-C₄alkoxy; R₁₅, R₁₆ and R₁₇ are each independently of the othersC₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈-alkynyl, or C₁-C₈alkyl mono-, di- ortri-substituted by halogen; —CN or by C₁-C₄alkoxy; R₁₈ is hydrogen orC₁-C₈alkyl; R₁₉ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono-, di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; or R₁₈ and R₁₉ together are a C₂-C₅alkylene chainwhich may be interrupted by an oxygen or sulfur atom; R₂₀ is hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it beingpossible for phenyl and benzyl in turn to be mono-, di- ortri-substituted by halogen C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN,—NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₂₁is hydrogen or C₁-C₈alkyl; R₂₂ is hydrogen or C₁-C₈alkyl, or isC₁-C₈alkyl mono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonylor by —CN, or R₂₂ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, itbeing possible for phenyl and benzyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;or R₂₁ and R₂₂ together are C₂-C₅alkylene; R₂₃ is hydrogen, C₁-C₄alkyl,C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₂₄ is hydrogen, C₁-C₄alkyl,C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₂₅ is hydrogen, C₁-C₈alkyl,C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₄haloalkyl or C₃-C₆haloalkenyl; R₂₆ ishydrogen or C₁-C₈alkyl; R₂₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkylmono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN,or R₂₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it beingpossible for phenyl and benzyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;or R₂₆ and R₂₇ together are C₂-C₅alkylene; R₂₈ is hydrogen orC₁-C₈alkyl; R₂₉ and R₃₀ are each independently of the other hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or C₁-C₆alkyl mono-, di- ortri-substituted by halogen, —CN or by C₁-C₄alkoxy; R₃₁ and R₃₂ are eachindependently of the other C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, orC₁-C₈alkyl mono-, di- or tri-substituted by halogen, —CN or byC₁-C₄alkoxy; m is 0, 1, 2, 3 or 4; each R₂ independently is hydrogen,halogen, —CN, —SCN, —CON, —N₃, —SF₅, —NO₂, —NR₃₃R₃₄, —CO₂R₃₅,—CONR₃₆R₃₇, —C(R₃₈)═NOR₃₉, —COR₄₀, —OR₄₁; —SR₄₂, —SOR₄₃, —SO₂R₄₄,—OSO₂R₄₅, —N([CO]_(p)R₄₆)COR₄₇, —N(OR₅₄)COR₅₅, —N(R₅₆)SO₂R₅₇,—N(SO₂R₅₈)SO₂R₅₉, —N═C(OR₆₀)R₆₁, —CR₆₂(OR₆₃)OR₆₄, —OC(O)NR₆₅R₆₆,—SC(O)NR₆₇R₆₈, —OC(S)NR₆₉R₇₀ or —N-phthalimide; or R₂ is a 5- to7-membered heterocylic ring system which may be aromatic or partially orfully saturated and may contain from 1 to 4 hetero atoms selected fromnitrogen, oxygen and sulfur, it being possible for that heterocyclicring system in turn to be mono-, di- or tri-substituted by halogen,C₁-C₄alkyl, C₁-C₄haloalkyl, hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy,C₁-C₄alkoxy-C₁-C₄alkyl, —CN, —NO₂, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl orby C₁-C₆alkylsulfonyl; R₃₃ is hydrogen or C₁-C₈alkyl; and R₃₄ ishydrogen, C₁-C₈alkyl; C₃-C₈alkenyl, C₃-C₈alkynyl; phenyl or benzyl, itbeing possible for phenyl and benzyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;or R₃₃ and R₃₄ together are a C₂-C₅alkylene chain which may beinterrupted by an oxygen or sulfur atom; R₃₅ is hydrogen, C₁-C₈alkyl,C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl, C₃-C₈alkenyl orC₃-C₈alkynyl mono-, di- or tri-substituted by halogen, C₁-C₄alkoxy or byphenyl, it being possible for phenyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄-haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;R₃₆ is hydrogen or C₁-C₈alkyl; R₃₇ is hydrogen or C₁-C₈alkyl, or isC₁-C₈alkyl mono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonylor by —CN, or R₃₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, itbeing possible for phenyl and benzyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;or R₃₆ and R₃₇ together are C₃-C₅alkylene; R₃₈ is hydrogen, C₁-C₄alkyl,C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₃₉ is hydrogen, C₁-C₈alkyl,C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₄haloalkyl or C₃-C₆haloalkenyl; R₄₀ ishydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₈alkylthio,—C(O)—C(O)OC₁-C₄alkyl or C₃-C₆cycloalkyl; R₄₁ is hydrogen, C₁-C₈alkyl,C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₈alkylcarbonyl,C₁-C₈alkoxycarbonyl, C₃-C₈alkenyloxycarbonyl,C₁-C₆alkoxy-C₁-C₆alkoxycarbonyl, C₁-C₆alkylthio-C₁-C₆alkyl,C₁-C₆alkylsulfinyl-C₁-C₆alkyl or C₁-C₆alkylsulfonyl-C₁-C₆alkyl; or R₄₁is phenyl or phenyl-C₁-C₆alkyl, it being possible for the phenyl ring inturn to be mono-, di- or tri-substituted by halogen, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂ or by —S(O)₂C₁-C₈alkyl, or R₄₁ isC₁-C₈alkyl mono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl,C₁-C₆alkylamino, di(C₁-C₆alkyl)amino or by —CN; R₄₂ is hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl mono-, di- ortri-substituted by halogen, —CN or by C₁-C₄alkoxy; R₄₃ and R₄₄ are eachindependently of the other C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, orC₁-C₈alkyl mono-, di- or tri-substituted by halogen, —CN or byC₁-C₄alkoxy; R₄₅ is C₁-C₈alkyl, C₁-C₈-alkyl mono-, di- ortri-substituted by halogen, —CN or by C₁-C₄alkoxy, or is C₃-C₈alkenyl orC₃-C₈alkynyl, or R₄₅ is phenyl, it being possible for the phenyl ring tobe mono-, di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, NO₂, C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or byC₁-C₈alkylsulfonyl; R₄₆ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl or C₁-C₄haloalkyl; R₄₇ is hydrogen, C₁-C₈alkyl,C₁-C₄alkoxy, C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl mono-, di-or tri-substituted by halogen, —CN, C₁-C₄alkoxy, C₁-C₈alkoxycarbonyl,—NH₂, C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, —NR₄₈COR₄₉, —NR₅₀SO₂R₅₁ orby —NR₅₂CO₂R₅₃, or R₄₇ is phenyl or benzyl, it being possible for phenyland benzyl in turn to be mono-, di- or tri-substituted by halogen,C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; p is 0 or 1; R₄₈, R₄₉, R₅₀,R₅₁, R₅₂ and R₅₃ are each independently of the others hydrogen,C₁-C₈alkyl, phenyl, benzyl or naphthyl, it being possible for the threelast-mentioned aromatic radicals in turn to be mono-, di- ortri-substituted by halogen, C₁-C₈alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₅₄ and R₅₅ are eachindependently of the other hydrogen, C₁-C₈alkyl, or phenyl which may inturn be mono-, di- or tri-substituted by halogen, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₈alkylthio,C₁-C₈alkylsulfinyl or by C₁-C₈alkylsulfonyl; R₅₆ is hydrogen,C₁-C₈alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₃-C₈alkenyl, C₃-C₈alkynyl orbenzyl, it being possible for benzyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₈alkylthio, C₁-C₈alkylsulfinyl or by C₁-C₈alkylsulfonyl;R₅₇ is C₁-C₈alkyl, C₁-C₄haloalkyl, phenyl, benzyl or naphthyl, it beingpossible for the last three aromatic rings to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₅₈ and R₅₉ are eachindependently of the other C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl, benzyl or naphthyl, it being possible for the last threearomatic rings to be mono-, di- or tri-substituted by halogen,C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄alkylamino,di(C₁-C₄alkyl)amino, —NH₂, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinylor by C₁-C₄alkylsulfonyl; R₆₀ and R₆₁ are each independently of theother hydrogen or C₁-C₆alkyl; R₆₂, R₆₃ and R₆₄ are each independently ofthe others hydrogen or C₁-C₈alkyl, or R₆₃ and R₆₄ together form aC₂-C₅alkylene bridge; R₆₅, R₆₆, R₆₇, R₆₈, R₆₉ and R₇₀ are eachindependently of the others hydrogen or C₁-C₈alkyl, or R₆₅ and R₆₆, orR₆₇ and R₆₈, or R₆₉ and R₇₀ in each case together form a C₂-C₅alkylenebridge; or each R₂ independently is C₁-C₈alkyl, or is C₁-C₈alkyl mono-,di- or tri-substituted by halogen, —CN, —N₃, —SCN, —NO₂, —NR₇₁R₇₂,—CO₂R₇₃, —CONR₇₄R₇₅, —COR₇₆, —C(R₇₇)═NOR₇₈, —C(S)NR₇₉R₈₀,—C(C₁-C₄alkylthio)═NR₈₁, —OR₈₂, —SR₈₃, —SOR₈₄, —SO₂R₈₅, —O(SO₂)R₈₆,—N(R₈₇)CO₂R₈₈, —N(R₈₉)COR₉₀, —S⁺(R₉₁)₂, —N⁺(R₉₂)₃, —Si(R₉₃)₃ or byC₃-C₆cycloalkyl; or each R₂ independently is C₁-C₈alkyl substituted by a5- to 7-membered heterocyclic ring system which may be aromatic orpartially or fully saturated and may contain from 1 to 4 hetero atomsselected from nitrogen, oxygen and sulfur, it being possible for thathetero-cyclic ring system in turn to be mono-, di- or tri-substituted byhalogen, C₁-C₄alkyl, C₁-C₄haloalkyl, hydroxy-C₁-C₄alkyl, C₁-C₄alkoxy,C₁-C₄alkoxy-C₁-C₄alkyl, —CN, —NO₂, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl orby C₁-C₆alkylsulfonyl; or each R₂ independently is C₂-C₈alkenyl, or isC₂-C₈alkenyl mono-, di- or tri-substituted by —CN, —NO₂, —CO₂R₉₄,—CONR₉₅R₉₆, —COR₉₇, —C(R₉₈)═NOR₉₉, —C(S)NR₁₀₀R₁₀₁,—C(C₁-C₄alkylthio)═NR₁₀₂, —OR₁₀₃, —Si(R₁₀₄)₃ or by C₃-C₆cycloalkyl; oreach R₂ independently is C₂-C₈alkynyl, or is C₂-C₈alkynyl mono-, di- ortri-substituted by halogen, —CN, —CO₂R₁₀₅, —CONR₁₀₆R₁₀₇, —COR₁₀₈,—C(R₁₀₉)═NOR₁₁₀, —C(S)NR₁₁₁R₁₁₂, —C(C₁-C₄alkylthio)═NR₁₁₃, —OR₁₁₄,—Si(R₁₁₅)₃ or by C₃-C₆cycloalkyl; or each R₂ independently isC₃-C₆cycloalkyl, or is C₃-C₆cycloalkyl mono-, di- or tri-substituted byhalogen, —CN, —CO₂R₁₁₆, —CONR₁₁₇R₁₁₈, —COR₁₁₉, —C(R₁₂₀)═NOR₁₂₁,—C(S)NR₁₂₂R₁₂₃ or by —C(C₁-C₄alkylthio)═NR₁₂₄; or two adjacent R₂substituents together form a C₁-C₇alkylene bridge which may beinterrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogenand sulfur and may be mono-, di- or tri-substituted by halogen,C₁-C₆alkyl or by C₁-C₆alkoxy, the total number of ring atoms being atleast 5 and at most 9; or two adjacent R₂ substituents together form aC₂-C₇alkenylene bridge which may be interrupted by from 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur and may be mono-, di- ortri-substituted by halogen, C₁-C₆alkyl or by C₁-C₆alkoxy, the totalnumber of ring atoms being at least 5, and at most 9; R₇₁ is hydrogen orC₁-C₈alkyl; R₇₂ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono-, di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; or R₇₁ and R₇₂ together are a C₂-C₅alkylene chainwhich may be interrupted by an oxygen or sulfur atom; R₇₃ is hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl, C₃-C₈alkenylor C₃-C₈alkynyl mono-, di- or tri-substituted by halogen, C₁-C₄alkoxy orby phenyl, it being possible for phenyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄-haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;R₇₄ is hydrogen or C₁-C₈alkyl; R₇₅ is hydrogen, C₁-C₈alkyl orC₃-C₇cycloalkyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by—COOH, C₁-C₈alkoxycarbonyl, C₁-C₆alkoxy or by —CN; or R₇₅ isC₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being possible forphenyl and benzyl in turn to be mono-, di- or tri-substituted byhalogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₇₄ andR₇₅ together are a C₂-C₅alkylene chain which may be interrupted by anoxygen or sulfur atom; R₇₆ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl orC₃-C₆cycloalkyl; R₇₇ is hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl orC₃-C₆cycloalkyl; R₇₈ is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl,C₃-C₈alkynyl, C₁-C₄haloalkyl or C₃-C₆haloalkenyl; and R₇₉ is hydrogen orC₁-C₈alkyl; R₈₀ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di-or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN, or R₈₀ isC₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being possible forphenyl and benzyl in turn to be mono-, di- or tri-substituted byhalogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₇₉ andR₈₀ together are C₂-C₅alkylene; R₈₁ is hydrogen or C₁-C₈alkyl; R₈₂ is—Si(C₁-C₆alkyl)₃, C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl whichis mono-, di- or tri-substituted by halogen, —CN, —NH₂, C₁-C₆alkylamino,di(C₁-C₆alkyl)amino or by C₁-C₄alkoxy; R₈₃ is hydrogen, C₁-C₈alkyl,C₃-C₈alkenyl or C₃-C₈alkynyl, or is C₁-C₈alkyl which is mono-, di- ortri-substituted by halogen, —CN, —NH₂, C₁-C₆alkylamino,di(C₁-C₆alkyl)amino or by C₁-C₄alkoxy; R₈₄, R₈₅ and R₈₆ are eachindependently of the others c₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈-alkynyl,or C₁-C₈alkyl which is mono-, di- or tri-substituted by halogen, —CN orby C₁-C₄-alkoxy; R₈₇ and R₈₉ are each independently of the otherhydrogen, C₁-C₈alkyl or C₁-C₈alkoxy; R₈₈ is C₁-C₈alkyl; R₉₀ is hydrogenor C₁-C₈alkyl; R₉₁ is C₁-C₄alkyl; R₉₂ and R₉₃ are each independently ofthe other C₁-C₆alkyl; R₉₄ is hydrogen, or is C₁-C₈alkyl, C₃-C₈alkenyl orC₃-C₈alkynyl, each of which may be mono-, di- or tri-substituted byhalogen, C₁-C₄alkoxy or by phenyl, it being possible for phenyl in turnto be mono-, di- or tri-substituted by halogen, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₉₅ is hydrogen orC₁-C₈alkyl; R₉₆ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkyl mono-, di-or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN; or R₉₆ isC₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it being possible forphenyl and benzyl in turn to be mono-, di- or tri-substituted byhalogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; or R₉₅ andR₉₆ together are C₂-C₅alkylene; R₉₇ and R₉₈ are each independently ofthe other hydrogen, C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₉₉is hydrogen, C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₄haloalkyl orC₃-C₆haloalkenyl; R₁₀₀ is hydrogen or C₁-C₈alkyl; R₁₀₁ is hydrogen orC₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by —COOH,C₁-C₈alkoxycarbonyl or by —CN; or R₁₀₁ is C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono-, di- or tri-substituted by halogen; C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio; C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; or R₁₀₀ and R₁₀₁ together are C₂-C₅alkylene; R₁₀₂ ishydrogen or C₁-C₈alkyl; R₁₀₃ is hydrogen, C₁-C₈alky, —Si(C₁-C₆alkyl)₃,C₃-C₈alkenyl or C₃-C₈alkynyl; R₁₀₄ is C₁-C₆alkyl; R₁₀₅ is hydrogen or isC₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, each of which may be mono-,di- or tri-substituted by halogen, C₁-C₄alkoxy or by phenyl, it beingpossible for phenyl in turn to be mono-, di- or tri-substituted byhalogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsufinyl or by C₁-C₄alkylsulfonyl; R₁₀₆ ishydrogen or C₁-C₈alkyl; R₁₀₇ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkylmono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN,or R₁₀₇ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it beingpossible for phenyl and benzyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;or R₁₀₆ and R₁₀₇ together are C₂-C₅alkylene; R₁₀₈ is hydrogen,C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₁₀₉ is hydrogen,C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₁₁₀ is hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₄haloalkyl orC₃-C₆haloalkenyl; R₁₁₁ is hydrogen or C₁-C₈alkyl; R₁₁₂ is hydrogen orC₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by —COOH,C₁-C₈alkoxycarbonyl or by —CN; or R₁₁₂ is C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono-, di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; or R₁₁₁ and R₁₁₂ together are C₂-C₅alkylene; R₁₁₃ ishydrogen or C₁-C₈alkyl; R₁₁₄ is hydrogen, C₁-C₈alkyl, —Si(C₁-C₆alkyl)₃,C₃-C₈alkenyl or C₃-C₈alkynyl; R₁₁₅ is C₁-C₆alkyl; R₁₁₆ is hydrogen or isC₁-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, each of which may be mono-,di- or tri-substituted by halogen, C₁-C₄alkoxy or by phenyl, it beingpossible for phenyl in turn to be mono-, di- or tri-substituted byhalogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, —CN, —NO₂,C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl; R₁₁₇ ishydrogen or C₁-C₈alky; R₁₁₈ is hydrogen or C₁-C₈alkyl, or is C₁-C₈alkylmono-, di- or tri-substituted by —COOH, C₁-C₈alkoxycarbonyl or by —CN;or R₁₁₈ is C₃-C₈alkenyl, C₃-C₈alkynyl, phenyl or benzyl, it beingpossible for phenyl and benzyl in turn to be mono-, di- ortri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,—CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or by C₁-C₄alkylsulfonyl;or R₁₁₇ and R₁₁₈ together are C₂-C₅alkylene; R₁₁₉ is hydrogen,C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₁₂₀ is hydrogen,C₁-C₄alkyl, C₁-C₄haloalkyl or C₃-C₆cycloalkyl; R₁₂₁ is hydrogen,C₁-C₈alkyl, C₃-C₈alkenyl, C₃-C₈alkynyl, C₁-C₄haloalkyl orC₃-C₆haloalkenyl; R₁₂₂ is hydrogen or C₁-C₈alkyl; R₁₂₃ is hydrogen orC₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by —COOH,C₁-C₈alkoxycarbonyl or by —CN; or R₁₂₃ is C₃-C₈alkenyl, C₃-C₈alkynyl,phenyl or benzyl, it being possible for phenyl and benzyl in turn to bemono-, di- or tri-substituted by halogen, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, —CN, —NO₂, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or byC₁-C₄alkylsulfonyl; or R₁₂₂ and R₁₂₃ together are C₂-C₅alkylene; andR₁₂₄ is hydrogen or C₁-C₈alkyl.
 3. A compound according to claim 2,wherein each R₁ independently is halogen, —CN, —NO₂, —C(R₁₀)═NOR₁₁,—OR₁₃, —SO₂R₁₆, —OSO₂R₁₇, C₁-C₈alkyl or C₂-C₈alkenyl, or is C₁-C₈alkylmono-, di- or tri-substituted by halogen or by —CN; R₁₀ is hydrogen orC₁-C₄alkyl; and R₁₁ is C₁-C₈alkyl.
 4. A compound according to claim 2,wherein Q is a group Q₁, Q₂, Q₃ or Q₅.
 5. A compound according to claim4, wherein Q is a group Q₁ or Q₂.
 6. A compound according to claim 2,wherein each R₂ independently is halogen, —CN, —SCN, —OCN, —N₃,—CONR₃₆R₃₇, —C(R₃₈)═NOR₃₉, —COR₄₀, —OR₄₁, —OSO₂R₄₅,—N([CO]_(p)R₄₆)COR₄₇, —N(R₅₆)SO₂R₅₇, —N(SO₂R₅₈)SO₂R₅₉, —N═C(OR₆₀)R₆₁ orC₁-C₈alkyl, or is C₁-C₈alkyl mono-, di- or tri-substituted by halogen,—CN, —N₃, —SCN, —CONR₇₄R₇₅, —COR₇₆, —C(R₇₇)═NOR₇₈, —C(S)NR₇₉R₈₀, —OR₈₂,—SOR₈₄, —SO₂R₈₅ or by —N(R₈₉)COR₉₀.
 7. A process for the preparation ofa compound of formula Ia

wherein R₁, R₂, R₃, R₄, Z, m and n are as defined in claim 1, whichprocess comprises reacting a compound of formula IIa

wherein R₁ and n are as defined in claim 1 (Q=Q₁) and X is halogen, witha compound of formula IIIa

wherein R₃ and R₄ are as defined in claim 1 and M⁺ is an alkali metalcation, to form a compound of formula IVa

wherein R₁, R₃, R₄ and n are as defined in claim 1, and then couplingthat compound with a compound of formula V

wherein Z, R₂ and m are as defined in claim 1 and A is a leaving group,in the presence of a palladium catalyst.
 8. A herbicidal andplant-growth-inhibiting composition which comprises on an inert carrier,a herbicidally effective amount of a compound of formula I.
 9. A methodof controlling undesired plant growth, which comprises applying aherbicidally effective amount of a compound of formula I or of acomposition comprising such a compound to the plants or to the locusthereof.
 10. A method of inhibiting plant growth, which comprisesapplying a herbicidally effective amount of a compound of formula I orof a composition comprising such a compound to the plants or to thelocus thereof.